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

HRID 1774408Notes

Reaction equation

HRID 1774408 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.C1(C)C=CC=CC=1.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 3

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

Product 1

HCID 14211262Benzyl 3-(4-hydroxyphenyl)propanoateYield 94.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-hydroxyphenyl)propionic acid (1.49 g, 8.96 mmol) in dimethylformamide (21.5 mL) were added potassium carbonate (1.30 g, 9.41 mmol) and benzyl bromide (1.69 g, 9.86 mmol), and the mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with toluene and water to separate the phases. The residue obtained by concentrating the organic layer under reduced pressure was subjected to silica gel column chromatography (hexane-ethyl acetate 5:1→3:1) to give 2.16 g of benzyl 3-(4-hydroxyphenyl)propionate as oil (yield: 94%).

Workup

  1. customto separate the phases
  2. customThe residue obtained
  3. concentrationby concentrating the organic layer under reduced pressure

Sources & evidence

ORD record
ord-2a325eaa36404e499850475773ce2e49
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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