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

HRID 327959

반응식

HRID 327959 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a11c6f641f1646b3bc98b5ca05bb82fc
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273999

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