Benzyl Bromide → 4-Hydroxy-2,2-dimethyl-butyric acid benzyl ester

HRID 1289872

Reaction equation

HRID 1289872 reaction equation
[K+].[OH:2][CH2:3][CH2:4][C:5]([CH3:10])([CH3:9])[C:6]([O-:8])=[O:7].[C:11]1([CH2:17]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C=O)C>[C:11]1([CH2:17][O:7][C:6](=[O:8])[C:5]([CH3:10])([CH3:9])[CH2:4][CH2:3][OH:2])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 23712640Potassium 4-hydroxy-2,2-dimethylbutyrate

Product 1

HCID 141523044-Hydroxy-2,2-dimethyl-butyric acid benzyl esterYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxy-2,2-dimethylbutyric acid monopotassium salt (10.6 g,62.35 mmol) and phenylmethyl bromide (11.63 g, 68 mmol) in 100 ml of DMF was stirred at room temperature for 24 hours and then the mixture was poured into ice/water. The mixture was extracted with ether (3×) and the organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (silica, 12-66% of ethyl acetate/hexane) to afford 10.02 g (72%) of 4-hydroxy-2,2-dimethylbutyric acid phenylmethyl ester.

Workup

  1. extractionThe mixture was extracted with ether (3×)
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica, 12-66% of ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1c8f11f91bd54ba8b74aafa15554c51d
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Linked notes

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