Benzyl Bromide → Methyl 3-(benzyloxy)-2,2-dimethylpropanoate

HRID 1802414Notes

Reaction equation

HRID 1802414 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][OH:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH3:3][O:4][C:5](=[O:11])[C:6]([CH3:10])([CH3:9])[CH2:7][O:8][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 59267989Methyl 3-(benzyloxy)-2,2-dimethylpropanoateYield 59.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% Sodium hydride in mineral oil (2.3 g, 56.8 mmol) is added to a solution of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (5.0 g, 37.8 mmol) in THF (80 mL) at 0° C., followed by the addition of benzylbromide (7.3 g, 42.6 mmol). The reaction mixture is slowly brought to room temperature, stirred for 8 h and then quenched with ice water and extracted with ethyl acetate. The organic phase is washed with water and brine, dried over Na2SO4 filtered and concentrated. The crude product is purified by column chromatography to afford 5.0 g of 3-benzyloxy-2,2-dimethyl-propionic acid methyl ester as a brown liquid; m/z 223 [M+H].

Workup

  1. customis slowly brought to room temperature
  2. customquenched with ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-e90142b9b6114dd59f9ec51818abf8e4
Source dataset
uspto-grants-2013_01
Patent number
US08349871B2

Reaction notes

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