Methyl 3-oxo-3-phenylpropanoate → Methyl 3-hydroxy-3-phenylpropanoate

HRID 2270890Notes

Reaction equation

HRID 2270890 reaction equation
[C:1]([CH2:9][C:10]([O:12][CH3:13])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[C:2]1([CH:1]([OH:8])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 348462Methyl 3-oxo-3-phenylpropanoate

Product 1

HCID 347841Methyl 3-hydroxy-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A2.3 mg (0.0014 mmol) portion of the thus obtained complex, 0.5 g (2.8 mmol) of methyl benzoylacetate and 2 ml of methanol were put into a stainless steel autoclave and stirred at 50° C. for 14 hours under a hydrogen pressure of 30 atm to obtain optically active methyl 3-phenyl-3-hydroxypropionate. When measured by HPLC, the conversion ratio was 100% and its optical purity was 96.5% ee.

Sources & evidence

ORD record
ord-10965dd10d6d4cff8e4509d546f6d77f
Source dataset
uspto-grants-2001_12
Patent number
US06333291B1

Reaction notes

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