Benzyl Bromide → Benzyl 3-(4-hydroxyphenyl)propanoate

HRID 516891Notes

Reaction equation

HRID 516891 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[OH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]([O:20][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:19])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 11430Potassium Carbonate

Product 1

HCID 14211262Benzyl 3-(4-hydroxyphenyl)propanoateYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (5.7 g, 33.09 mmol) was added to a suspension of 3-(4-hydroxyphenyl)propanoic acid (5.0 g, 30.08 mmol) and anhydrous potassium carbonate (8.31 g, 60.17 mmol) in anhydrous DMF (60 ml), and the mixture was stirred for 15 hr. The reaction mixture was diluted with water and was extracted with ethyl acetate, and the organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate=8:2) to give the title compound as an oil (6.8 g, yield 88%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washthe organic layer was washed with saturated brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed on silica gel column (hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-fc731761bfaa4b44bafefcd303310845
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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