Benzyl Bromide → HCID 57457873, compound

HRID 1821690Notes

Reaction equation

HRID 1821690 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11](=[O:13])[CH3:12].[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11](=[O:13])[CH3:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23013943HCID 23013943, compound

Product 1

HCID 57457873HCID 57457873, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (8 mL) was dissolved 2.00 g (11.2 mmol) of 1-(2-hydroxy-3,4,6-trimethylphenyl)ethanone obtained in Example 622 (2). To the solution was added in an ice bath 0.488 g (11.2 mmol) of 60% sodium hydride, and after stirring in an ice bath for 10 minutes, 1.92 g (11.2 mmol) of benzyl bromide was gradually added dropwise and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 2.36 g (8.81 mmol, Yield: 78.7%) of 1-[2-(benzyloxy)-3,4,6-trimethylphenyl]ethanone.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)

Sources & evidence

ORD record
ord-802d115498c941cd9a3600b81adbac8e
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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