Phenylacetone → ethyl 3-hydroxy-3-methyl-4-phenylbutanoate

HRID 1589729Notes

Reaction equation

HRID 1589729 reaction equation
[CH3:1][C:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C=CC=CC=1.[Zn]>[OH:3][C:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:1])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 7678PhenylacetoneHCID 7748Ethyl bromoacetate

Product 1

HCID 288210ethyl 3-hydroxy-3-methyl-4-phenylbutanoateYield 68.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

A mixture of benzyl methyl ketone (134 g, 1 mole) and ethyl bromoacetate (168 g, 1 mole) was added to a mixture of mossy zinc (100 g) in toluene (500 cm3) in a large flask. When the vigorous exothermic reaction had subsided, the mixture was boiled for 3 hours. The solution was cooled, and washed sequentially with dilute sulfuric acid, 10% aqueous sodium hydroxide and then with water. The organic layer was separated, dried and filtered. The toluene solvent was removed, leaving the hydroxy ester, ethyl 3-hydroxy-3-benzylbutanoate (152.8 g), as an orange oil. The ester's structure and purity were established by NMR spectroscopy.

Workup

  1. customWhen the vigorous exothermic reaction
  2. temperatureThe solution was cooled
  3. washwashed sequentially with dilute sulfuric acid, 10% aqueous sodium hydroxide
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customThe toluene solvent was removed

Sources & evidence

ORD record
ord-ecdf993ddfc34613a54c26dda15168f3
Source dataset
uspto-grants-1993_04
Patent number
US05200116

Reaction notes

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