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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
US08530647B2

Procedure details

A suspension of 10 g of iminostilbene in 100 ml toluene was treated with 20.2 g of sodium cyanate and 27.5 g of mandelic acid and was heated to reflux for about 10 hrs. The reaction mixture was cooled to room temperature and charged with sodium hydroxide solution and maintained for 8 hrs. The resulting suspension was filtered, washed with water and dried to give 11 g of carbamazepine.
Quantity
10 g
Type
reactant
Reaction Step One
Quantity
100 mL
Type
solvent
Reaction Step One
Name
sodium cyanate
Quantity
20.2 g
Type
reactant
Reaction Step Two
Quantity
27.5 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[O-:16][C:17]#[N:18].[Na+].C(O)(=O)C(C1C=CC=CC=1)O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:17]([NH2:18])=[O:16])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1 |f:1.2,4.5|

Inputs

Step One
Name
Quantity
10 g
Type
reactant
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2
Name
Quantity
100 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Step Two
Name
sodium cyanate
Quantity
20.2 g
Type
reactant
Smiles
[O-]C#N.[Na+]
Name
Quantity
27.5 g
Type
reactant
Smiles
C(C(O)C1=CC=CC=C1)(=O)O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
was heated
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for about 10 hrs
Duration
10 h
TEMPERATURE
Type
TEMPERATURE
Details
maintained for 8 hrs
Duration
8 h
FILTRATION
Type
FILTRATION
Details
The resulting suspension was filtered
WASH
Type
WASH
Details
washed with water
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2C(=O)N
Measurements
Type Value Analysis
AMOUNT: MASS 11 g
YIELD: CALCULATEDPERCENTYIELD 90%

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
US08530647B2

Procedure details

A suspension of 10 g of iminostilbene in 100 ml toluene was treated with 20.2 g of sodium cyanate and 27.5 g of mandelic acid and was heated to reflux for about 10 hrs. The reaction mixture was cooled to room temperature and charged with sodium hydroxide solution and maintained for 8 hrs. The resulting suspension was filtered, washed with water and dried to give 11 g of carbamazepine.
Quantity
10 g
Type
reactant
Reaction Step One
Quantity
100 mL
Type
solvent
Reaction Step One
Name
sodium cyanate
Quantity
20.2 g
Type
reactant
Reaction Step Two
Quantity
27.5 g
Type
reactant
Reaction Step Two
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three

Identifiers

REACTION_CXSMILES
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.[O-:16][C:17]#[N:18].[Na+].C(O)(=O)C(C1C=CC=CC=1)O.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:1]1[CH:2]=[CH:3][C:4]2[N:15]([C:17]([NH2:18])=[O:16])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1 |f:1.2,4.5|

Inputs

Step One
Name
Quantity
10 g
Type
reactant
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2
Name
Quantity
100 mL
Type
solvent
Smiles
C1(=CC=CC=C1)C
Step Two
Name
sodium cyanate
Quantity
20.2 g
Type
reactant
Smiles
[O-]C#N.[Na+]
Name
Quantity
27.5 g
Type
reactant
Smiles
C(C(O)C1=CC=CC=C1)(=O)O
Step Three
Name
Quantity
0 (± 1) mol
Type
reactant
Smiles
[OH-].[Na+]

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

TEMPERATURE
Type
TEMPERATURE
Details
was heated
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for about 10 hrs
Duration
10 h
TEMPERATURE
Type
TEMPERATURE
Details
maintained for 8 hrs
Duration
8 h
FILTRATION
Type
FILTRATION
Details
The resulting suspension was filtered
WASH
Type
WASH
Details
washed with water
CUSTOM
Type
CUSTOM
Details
dried

Outcomes

Product
Name
Type
product
Smiles
C=1C=CC2=C(C1)C=CC=3C=CC=CC3N2C(=O)N
Measurements
Type Value Analysis
AMOUNT: MASS 11 g
YIELD: CALCULATEDPERCENTYIELD 90%

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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