Benzyl Bromide → Benzyl 4-hydroxymethylphenylacetate

HRID 977888Notes

Reaction equation

HRID 977888 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:18]=1>CN(C)C=O.C(OCC)C>[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:25])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 32834984-(Hydroxymethyl)phenylacetic acid

Product 1

HCID 19966265Benzyl 4-hydroxymethylphenylacetateYield 82.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

2.52 g (23.8 mmol) of sodium carbonate and 8.13 g (47.6 mmol) of benzyl bromide were added to a solution of 3.95 g (23.8 mmol) of 4-Hydroxymethylphenylacetic acid [prepared as described in step (i) above] in 40 ml of N,N-dimethylformamide, and the resulting mixture was stirred for 3.5 hours. At the end of this time, the reaction mixture was diluted with diethyl ether, and the diluted mixture was washed with water and then with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified by column chromatography through 200 g of silica gel, using a gradient elution method, with mixtures of methylene chloride and ethyl acetate in ratios ranging from 100:5 to 100:10 by volume as the eluent, to give 5.03 g (yield 82%) of the title compound as an oil.

Workup

  1. washthe diluted mixture was washed with water
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by column chromatography through 200 g of silica gel
  5. washa gradient elution method

Sources & evidence

ORD record
ord-c977c3f245c6431a876b11e22a2a1518
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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