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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
US04259521

Procedure details

To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor obtained from resolution B, containing about 2.4 moles of a mixture of diastereomers, consisting of about 2.25 moles of (-)-2-amino-1-butanol L-(+)-mandelate and about 0.15 mole of (-)-2-amino-1-butanol D-(-)-mandelate, is added 180 grams of potassium hydroxide (88.8% real; 2.85 moles) to obtain a solution having an initial αD25°C. of +24.7° ("as is", 10 cm cell). The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours to obtain a mandelic acid solution having an αD25°C. of -3.0° ("as is", 10 cm cell). The resulting solution is essentially racemized, the negative rotation being due to the presence of the (-)-2-amino-1-butanol.
[Compound]
Name
mixture
Quantity
2.4 mol
Type
reactant
Reaction Step One
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Reaction Step Two
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Reaction Step Three
Quantity
180 g
Type
reactant
Reaction Step Four

Identifiers

REACTION_CXSMILES
[C:1]([O:11]CC(N)CC)(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C(OCC(N)CC)(=O)[C@@H](C1C=CC=CC=1)O.[OH-].[K+]>>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3] |f:2.3|

Inputs

Step One
Name
mixture
Quantity
2.4 mol
Type
reactant
Smiles
Step Two
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Smiles
C([C@@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
Step Three
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Smiles
C([C@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
Step Four
Name
Quantity
180 g
Type
reactant
Smiles
[OH-].[K+]

Conditions

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

Workups

WASH
Type
WASH
Details
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor
CUSTOM
Type
CUSTOM
Details
obtained from resolution B
CUSTOM
Type
CUSTOM
Details
to obtain a solution
CUSTOM
Type
CUSTOM
Details
αD25°C. of +24.7° ("as is", 10 cm cell)
TEMPERATURE
Type
TEMPERATURE
Details
The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours
Duration
4 h

Outcomes

Product
Name
Type
product
Smiles
C(C(O)C1=CC=CC=C1)(=O)O

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
US04259521

Procedure details

To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor obtained from resolution B, containing about 2.4 moles of a mixture of diastereomers, consisting of about 2.25 moles of (-)-2-amino-1-butanol L-(+)-mandelate and about 0.15 mole of (-)-2-amino-1-butanol D-(-)-mandelate, is added 180 grams of potassium hydroxide (88.8% real; 2.85 moles) to obtain a solution having an initial αD25°C. of +24.7° ("as is", 10 cm cell). The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours to obtain a mandelic acid solution having an αD25°C. of -3.0° ("as is", 10 cm cell). The resulting solution is essentially racemized, the negative rotation being due to the presence of the (-)-2-amino-1-butanol.
[Compound]
Name
mixture
Quantity
2.4 mol
Type
reactant
Reaction Step One
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Reaction Step Two
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Reaction Step Three
Quantity
180 g
Type
reactant
Reaction Step Four

Identifiers

REACTION_CXSMILES
[C:1]([O:11]CC(N)CC)(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C(OCC(N)CC)(=O)[C@@H](C1C=CC=CC=1)O.[OH-].[K+]>>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3] |f:2.3|

Inputs

Step One
Name
mixture
Quantity
2.4 mol
Type
reactant
Smiles
Step Two
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Smiles
C([C@@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
Step Three
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Smiles
C([C@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
Step Four
Name
Quantity
180 g
Type
reactant
Smiles
[OH-].[K+]

Conditions

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

Workups

WASH
Type
WASH
Details
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor
CUSTOM
Type
CUSTOM
Details
obtained from resolution B
CUSTOM
Type
CUSTOM
Details
to obtain a solution
CUSTOM
Type
CUSTOM
Details
αD25°C. of +24.7° ("as is", 10 cm cell)
TEMPERATURE
Type
TEMPERATURE
Details
The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours
Duration
4 h

Outcomes

Product
Name
Type
product
Smiles
C(C(O)C1=CC=CC=C1)(=O)O

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
US04259521

Procedure details

To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor obtained from resolution B, containing about 2.4 moles of a mixture of diastereomers, consisting of about 2.25 moles of (-)-2-amino-1-butanol L-(+)-mandelate and about 0.15 mole of (-)-2-amino-1-butanol D-(-)-mandelate, is added 180 grams of potassium hydroxide (88.8% real; 2.85 moles) to obtain a solution having an initial αD25°C. of +24.7° ("as is", 10 cm cell). The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours to obtain a mandelic acid solution having an αD25°C. of -3.0° ("as is", 10 cm cell). The resulting solution is essentially racemized, the negative rotation being due to the presence of the (-)-2-amino-1-butanol.
[Compound]
Name
mixture
Quantity
2.4 mol
Type
reactant
Reaction Step One
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Reaction Step Two
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Reaction Step Three
Quantity
180 g
Type
reactant
Reaction Step Four

Identifiers

REACTION_CXSMILES
[C:1]([O:11]CC(N)CC)(=[O:10])[C@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].C(OCC(N)CC)(=O)[C@@H](C1C=CC=CC=1)O.[OH-].[K+]>>[C:1]([OH:11])(=[O:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3] |f:2.3|

Inputs

Step One
Name
mixture
Quantity
2.4 mol
Type
reactant
Smiles
Step Two
Name
(-)-2-amino-1-butanol L-(+)-mandelate
Quantity
2.25 mol
Type
reactant
Smiles
C([C@@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
Step Three
Name
(-)-2-amino-1-butanol D-(-)-mandelate
Quantity
0.15 mol
Type
reactant
Smiles
C([C@H](O)C1=CC=CC=C1)(=O)OCC(CC)N
Step Four
Name
Quantity
180 g
Type
reactant
Smiles
[OH-].[K+]

Conditions

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

Workups

WASH
Type
WASH
Details
To a portion (1100 mls out of a total of 4800 mls) of the mother liquor plus methanol wash liquor
CUSTOM
Type
CUSTOM
Details
obtained from resolution B
CUSTOM
Type
CUSTOM
Details
to obtain a solution
CUSTOM
Type
CUSTOM
Details
αD25°C. of +24.7° ("as is", 10 cm cell)
TEMPERATURE
Type
TEMPERATURE
Details
The solution is then heated at 115°-116° C. under pressure (40 psi) for 4 hours
Duration
4 h

Outcomes

Product
Name
Type
product
Smiles
C(C(O)C1=CC=CC=C1)(=O)O

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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