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molecular formula C8H8O3 B119166 (S)-(+)-Mandelic acid CAS No. 17199-29-0

(S)-(+)-Mandelic acid

Cat. No. B119166
M. Wt: 152.15 g/mol
InChI Key: IWYDHOAUDWTVEP-UHFFFAOYSA-N
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Patent
US04983771

Procedure details

To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.
Quantity
201 g
Type
reactant
Reaction Step One
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
305.4 g
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[OH-].[Na+].[C:3]([O-:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Na+].C([O-])(=O)C.[Na+].Cl>>[C:3]([OH:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5] |f:0.1,2.3.4.5|

Inputs

Step One
Name
Quantity
201 g
Type
reactant
Smiles
[OH-].[Na+]
Step Two
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(O)C1=CC=CC=C1)(=O)[O-].[Na+].C(C)(=O)[O-].[Na+]
Step Three
Name
Quantity
305.4 g
Type
reactant
Smiles
Cl

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The basic solution was extracted 3 times with toluene
ADDITION
Type
ADDITION
Details
for a total toluene addition of 325 grams
DISTILLATION
Type
DISTILLATION
Details
The toluene and (-)PEA were distilled off under vacuum
CUSTOM
Type
CUSTOM
Details
resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams
CUSTOM
Type
CUSTOM
Details
giving a pH of about 0.8
EXTRACTION
Type
EXTRACTION
Details
This was extracted 4 times with MIBK
ADDITION
Type
ADDITION
Details
in a fashion similar to that above, for a total addition of 295.3 grams MIBK
ADDITION
Type
ADDITION
Details
185 grams H2O was added to the MIBK
DISTILLATION
Type
DISTILLATION
Details
the MIBK was distilled off with azeotropic distillation
CUSTOM
Type
CUSTOM
Details
The mandelic acid recovered from this process
CUSTOM
Type
CUSTOM
Details
together with that recovered above,

Outcomes

Product
Name
Type
product
Smiles
C(C(O)C1=CC=CC=C1)(=O)O
Measurements
Type Value Analysis
AMOUNT: MASS 299.44 g

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04983771

Procedure details

To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.
Quantity
201 g
Type
reactant
Reaction Step One
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
305.4 g
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[OH-].[Na+].[C:3]([O-:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Na+].C([O-])(=O)C.[Na+].Cl>>[C:3]([OH:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5] |f:0.1,2.3.4.5|

Inputs

Step One
Name
Quantity
201 g
Type
reactant
Smiles
[OH-].[Na+]
Step Two
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(O)C1=CC=CC=C1)(=O)[O-].[Na+].C(C)(=O)[O-].[Na+]
Step Three
Name
Quantity
305.4 g
Type
reactant
Smiles
Cl

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The basic solution was extracted 3 times with toluene
ADDITION
Type
ADDITION
Details
for a total toluene addition of 325 grams
DISTILLATION
Type
DISTILLATION
Details
The toluene and (-)PEA were distilled off under vacuum
CUSTOM
Type
CUSTOM
Details
resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams
CUSTOM
Type
CUSTOM
Details
giving a pH of about 0.8
EXTRACTION
Type
EXTRACTION
Details
This was extracted 4 times with MIBK
ADDITION
Type
ADDITION
Details
in a fashion similar to that above, for a total addition of 295.3 grams MIBK
ADDITION
Type
ADDITION
Details
185 grams H2O was added to the MIBK
DISTILLATION
Type
DISTILLATION
Details
the MIBK was distilled off with azeotropic distillation
CUSTOM
Type
CUSTOM
Details
The mandelic acid recovered from this process
CUSTOM
Type
CUSTOM
Details
together with that recovered above,

Outcomes

Product
Name
Type
product
Smiles
C(C(O)C1=CC=CC=C1)(=O)O
Measurements
Type Value Analysis
AMOUNT: MASS 299.44 g

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US04983771

Procedure details

To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.
Quantity
201 g
Type
reactant
Reaction Step One
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Name
Quantity
305.4 g
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[OH-].[Na+].[C:3]([O-:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Na+].C([O-])(=O)C.[Na+].Cl>>[C:3]([OH:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5] |f:0.1,2.3.4.5|

Inputs

Step One
Name
Quantity
201 g
Type
reactant
Smiles
[OH-].[Na+]
Step Two
Name
sodium mandelate sodium acetate
Quantity
0 (± 1) mol
Type
reactant
Smiles
C(C(O)C1=CC=CC=C1)(=O)[O-].[Na+].C(C)(=O)[O-].[Na+]
Step Three
Name
Quantity
305.4 g
Type
reactant
Smiles
Cl

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

EXTRACTION
Type
EXTRACTION
Details
The basic solution was extracted 3 times with toluene
ADDITION
Type
ADDITION
Details
for a total toluene addition of 325 grams
DISTILLATION
Type
DISTILLATION
Details
The toluene and (-)PEA were distilled off under vacuum
CUSTOM
Type
CUSTOM
Details
resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams
CUSTOM
Type
CUSTOM
Details
giving a pH of about 0.8
EXTRACTION
Type
EXTRACTION
Details
This was extracted 4 times with MIBK
ADDITION
Type
ADDITION
Details
in a fashion similar to that above, for a total addition of 295.3 grams MIBK
ADDITION
Type
ADDITION
Details
185 grams H2O was added to the MIBK
DISTILLATION
Type
DISTILLATION
Details
the MIBK was distilled off with azeotropic distillation
CUSTOM
Type
CUSTOM
Details
The mandelic acid recovered from this process
CUSTOM
Type
CUSTOM
Details
together with that recovered above,

Outcomes

Product
Name
Type
product
Smiles
C(C(O)C1=CC=CC=C1)(=O)O
Measurements
Type Value Analysis
AMOUNT: MASS 299.44 g

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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