Succinic Acid → ethyl mandelate, (S)-

HRID 2166213Notes

Reaction equation

HRID 2166213 reaction equation
[C:1]1([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)CCC(O)=O>>[OH:13][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

3

Reactant 2

HCID 1110Succinic AcidHCID 15349Ethyl benzoylformate

Product 1

HCID 6951557ethyl mandelate, (S)-Yield 87%

Procedure

Ethyl phenylglyoxylate acid (0.5 g) was asymmetrically reduced in the same manner as in Example 19, except that 1.33 g (11.2 mmol) of succinic acid was used in place of benzoic acid, giving 0.44 g of ethyl (S)-(+)-2-hydroxy-2-phenylacetate, having a specific rotation [α]D18 of +19.4° (cl. 18, CHCl3). The synthesis yield was 87% and the optical yield was 15% e.e. (see Reference 7).

Sources & evidence

ORD record
ord-c215304da9ae4d939fee1e6d7da160b5
Source dataset
uspto-grants-1990_07
Patent number
US04943652

Reaction notes

Loading…