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

HRID 569504Notes

Reaction equation

HRID 569504 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][CH2:11][C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14].[K]>CN(C)C=O>[C:2]1([CH2:1][O:15][C:13](=[O:14])[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][OH:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 5462222PotassiumHCID 138845934-Hydroxy-2,2-dimethylbutanoic acid

Product 1

HCID 141523044-Hydroxy-2,2-dimethyl-butyric acid benzyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of benzyl bromide (37.4 g) and 4-hydroxy-2,2-dimethylbutanoic acid, monopotassium salt, (3.4 g) in dimethylformamide (35 mL) was stirred at room temperature for 18 hours. The precipitate was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel eluting with 2:1 dichloromethane:ethyl acetate to give 3.95 g (89%) of 4-hydroxy-2,2-dimethylbutanoic acid phenylmethyl ester as a colorless oil. A sample was evaporatively distilled to give the analytical sample: bp 160°-165° C./0.25 mm; IR (CHCl3) 3595 (OH), 1707 (C=O) and 687 cm-1 (C6H5); NMR (CDCl3) δ 1.23 (s, 6, CH3), 1.85 (t, 2, CH2), 3.67 (t, 2, CH2), 5.11 (s, 2, CH2) and 7.34 (s, 5, Ph); MS m/e 222,91.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel eluting with 2:1 dichloromethane

Sources & evidence

ORD record
ord-dd9289ba259d475ea522918319eda8f5
Source dataset
uspto-grants-1988_03
Patent number
US04732902

Reaction notes

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