Ethyl benzoylformate → (-)-Ethyl mandelate

HRID 2166210Notes

Reaction equation

HRID 2166210 reaction equation
[BH4-].[Na+].C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.[C:13]1([C:19](=[O:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[OH:25][C@H:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 15349Ethyl benzoylformateHCID 444305L-Tartaric acidHCID 4311764Sodium borohydride

Product 1

HCID 6951556(-)-Ethyl mandelate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a dispersion of 0.43 g (11.3 mmol) of sodium borohydride in THF (35 ml), there was added 1.70 g (11.3 mmol) of L-(+)-tartaric acid, and the mixture was heated under reflux for four hours in an oil bath at 70° C. with stirring. The resulting mixture was cooled in a cryostat at -20° C., a solution of 0.5 g (2.8 mmol) of ethyl phenylglyoxylate in THF (5 ml) was added dropwise over a period of ten minutes, and stirring was continued for 19 hours. The reaction mixture was treated in the same manner as in Example 6, giving 0.44 of ethyl (R)-(-)-2-hydroxy-2-phenylacetate, having a specific rotation [α]D16 of -109° (cl. 00, CHCl3).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe resulting mixture was cooled in a cryostat at -20° C.
  3. stirringstirring
  4. additionThe reaction mixture was treated in the same manner as in Example 6

Sources & evidence

ORD record
ord-23d7742559c24a7d8cf6c67f17defabd
Source dataset
uspto-grants-1990_07
Patent number
US04943652

Reaction notes

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