Benzyl Chloride → Methyl 3-(benzyloxy)benzoate

HRID 649332Notes

Reaction equation

HRID 649332 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 13368031Methyl 3-(benzyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1564 g. (10.2 mole) of methyl 3-hydroxybenzoate, 1407.6 g. (10.2 mole) potassium carbonate and 1285.2 g. (10.2 mole) benzyl chloride in 5 l. of acetone is heated at reflux for 22 hours. The reaction mixture is then cooled, filtered and the filtrate evaporated. The residue is crystallized in a small volume of pentane to give a quantitative yield of the title compound.

Workup

  1. additionA mixture of 1564 g
  2. temperatureat reflux for 22 hours
  3. temperatureThe reaction mixture is then cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customThe residue is crystallized in a small volume of pentane

Sources & evidence

ORD record
ord-f1d8cdba6a2c4df3881a092afd3fb97c
Source dataset
uspto-grants-1988_04
Patent number
US04739079

Reaction notes

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