Allyl bromide → 3-Chloromethyl-benzoic acid allyl ester

HRID 276720

Reaction equation

HRID 276720 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20]>CC(C)=O>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:8][CH2:20][CH:19]=[CH2:18])=[O:7]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2417523-(Chloromethyl)benzoic acid

Product 1

HCID 114243703-Chloromethyl-benzoic acid allyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-(chloromethyl)-benzoic acid (50.0 g, 0.293 mol), potassium carbonate (48.61 g, 0.352 mol) and allyl bromide (50.7 mL, 0.586 mol) in acetone (500 mL) is refluxed for 2 hours, after which time the solution was cooled to room temp. and filtered through celite. The filtrate is evaporated and the residue chromatographed (silica, 5% EtOAc/hexane) to yield allyl 3-(chloromethyl)-benzoate as a clear oil.

Workup

  1. temperatureafter which time the solution was cooled to room temp.
  2. filtrationfiltered through celite
  3. customThe filtrate is evaporated
  4. customthe residue chromatographed (silica, 5% EtOAc/hexane)

Sources & evidence

ORD record
ord-cf5788fce5884aba8062303175a062fa
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Linked notes

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