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Chloroacetyl chloride → Benzenepropanoic acid, 4-(chloroacetyl)-, methyl ester

HRID 483151
ノート
印刷プレビュー

反応式

HRID 483151 の反応式
[C:1]1([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Cl:13][CH2:14][C:15]([C:4]1[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:2][CH:3]=1)=[O:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 7643Methyl 3-phenylpropionateHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 10800114Benzenepropanoic acid, 4-(chloroacetyl)-, methyl ester収率 72.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A mixture of 50 g of methyl 3-phenylpropionate, 51.6 g of chloroacetyl chloride and 250 ml of dichloromethane was cooled to 0° C. The mixture was stirred at 0° to 10° C. and 122 g of aluminum chloride was added gradually into the mixture. The reaction mixture was then stirred at a room temperature for 2 hours. The reaction mixture was allowed to stand overnight, then the reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid and was extracted with chloroform. The chloroform layer was washed with water, dried then chloroform was removed from the reaction mixture by distillation. The residue thus obtained was crystallized by adding isopropyl ether, and the crystals formed were collected by filtration, then recrystallized from ethanol to obtain 53.4 g of methyl 3-(4-chloroacetylphenyl)propionate in the form of needle-like crystals.

後処理

  1. stirringThe reaction mixture was then stirred at a room temperature for 2 hours
  2. additionthe reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid
  3. extractionwas extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. customdried
  6. customchloroform was removed from the reaction mixture by distillation
  7. customThe residue thus obtained
  8. customwas crystallized
  9. additionby adding isopropyl ether
  10. customthe crystals formed
  11. filtrationwere collected by filtration
  12. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-4007806d8ad9416baa81c65d627ff823
出典データセット
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04578381

反応ノート

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