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

HRID 327959

反応式

HRID 327959 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a11c6f641f1646b3bc98b5ca05bb82fc
出典データセット
uspto-grants-1993_12
特許番号
US05273999

関連ノート

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