Acetonitrile → 2-[3-(Chloromethyl)phenylmethoxy]benzenepropanoic acid methyl ester

HRID 1647999Notes

Reaction equation

HRID 1647999 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].[Cl:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22]Cl)[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOCC>[CH3:1][O:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][Cl:14])[CH:17]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 12275Benzene, 1,3-bis(chloromethyl)-HCID 2794569Methyl 3-(2-hydroxyphenyl)propionate

Product 1

HCID 537171172-[3-(Chloromethyl)phenylmethoxy]benzenepropanoic acid methyl esterYield 54.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.8 g (10 mmol) of 2-hydroxybenzenepropanoic acid methyl ester, 14 g (80 mmol) of α,α'-dichloro-m-xylene, 4.25 g (30.8 mmol) of anhydrous, granular potassium carbonate, and 70 mL of acetonitrile was stirred and refluxed for 4 hr. After being cooled, the resulting mixture was diluted with 200 mL of ether and filtered with suction. The solids were washed thoroughly with ether and then the filtrate and washes were combined and concentrated in vacuo. The oily residue was chromatographed on 100 g of silica gel. Elution with 19:1 hexane-ether afforded 1.74 g (54.6%) of 2-[3-(chloromethyl)phenylmethoxy]benzenepropanoic acid methyl ester as a colorless oil.

Workup

  1. temperaturerefluxed for 4 hr
  2. temperatureAfter being cooled
  3. filtrationfiltered with suction
  4. washThe solids were washed thoroughly with ether
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was chromatographed on 100 g of silica gel
  7. washElution with 19:1 hexane-ether

Sources & evidence

ORD record
ord-66d7cabf6ae64bd3ae7ff3d35ce4e356
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

Loading…