Hydrochloric Acid → Methyl 2-(1-hydroxyethyl)-3-phenylpropionate

HRID 1646318Notes

Reaction equation

HRID 1646318 reaction equation
[C:1]([CH:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CO>[OH:3][CH:1]([CH:4]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10679785Methyl 2-benzyl-3-oxobutanoate

Product 1

HCID 15670376Methyl 2-(1-hydroxyethyl)-3-phenylpropionateYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 2-acetyl-3-phenylpropionate (60 g) is dissolved in methanol (300 ml), and thereto is added portionwise sodium boro hydride (2.9 g) with stirring under ice cooling, and the mixture is stirred under ice cooling from 2 hours. The reaction mixture is adjusted to pH 1 with 10% hydrochloric acid, and methanol is distilled off under reduced pressure. The residue is extracted with ethyl acetate. The extract is washed with diluted aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and ethyl acetate is distilled off under reduced pressure to give methyl 2-(1-hydroxyethyl)-3-phenylpropionate (60.4 g).

Workup

  1. stirringthe mixture is stirred under ice cooling from 2 hours
  2. distillationis distilled off under reduced pressure
  3. extractionThe residue is extracted with ethyl acetate
  4. washThe extract is washed with diluted aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate, and ethyl acetate
  6. distillationis distilled off under reduced pressure

Sources & evidence

ORD record
ord-4c853358f3144ce29179968eb468fa6c
Source dataset
uspto-grants-1993_01
Patent number
US05179125

Reaction notes

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