Benzyl Bromide → HCID 14281237, compound

HRID 867601Notes

Reaction equation

HRID 867601 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>O1CCCC1>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:8][C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)=[O:11])=[CH:6][CH:7]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

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

Product 1

HCID 14281237HCID 14281237, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-Hydroxyphenyl)propionic acid (5 g), potassium carbonate (16 g) and tetrahydrofuran (50 ml) were placed in a three-necked flask, 8.5 ml of benzyl bromide was added dropwise through a syringe under stirring, and the mixture was heated under reflux overnight. After filtering off the solid matters, the solvent was distilled off, and the residue was purified by column chromatography on silica gel (50 g), affording 9.25 g (89.3%) of pure benzyl 3-(4-benzyloxyphenyl)propionate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationAfter filtering off the solid matters
  4. distillationthe solvent was distilled off
  5. customthe residue was purified by column chromatography on silica gel (50 g)

Sources & evidence

ORD record
ord-8f6f6c880386459ea0522d24ad9b32f8
Source dataset
uspto-grants-1988_10
Patent number
US04775743

Reaction notes

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