4-Chlorobenzaldehyde → 2-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

HRID 327246

反応式

HRID 327246 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:12][CH2:13][CH3:14])=[O:11]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:15][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 77264-ChlorobenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

生成物 1

HCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 4-chlorobenzaldehyde (28 g) and (carboethoxymethylene)triphenylphosphorane (73 g) in toluene (500 mL) was refluxed for 2 hours. The reaction was cooled to room temperature and concentrated under vacuum to a total volume of 150 mL. Then pure hexane (500 mL) was added and the mixture was left for 18 hours at room temperature. The solid (triphexylphosphine oxide) was filtered, rinsed with hexane and the filtrate evaporated to give crude product which was distilled at 0.5 mm Hg, and the fraction boiling at 130° C. was collected to give ethyl 4-chlorocinnamate, which was reduced as follows: the cinnamate (21 g) was hydrogenated in EtoAc (300 mL) in the presence of 5% Pd on C (2 g) for 3 hours at atmospheric pressure. After completion, the reaction mixture was filtered through a celite pad, rinsed with EtOAc and the filtrate evaporated to dryness to give the title product as an oil.

後処理

  1. concentrationconcentrated under vacuum to a total volume of 150 mL
  2. additionThen pure hexane (500 mL) was added
  3. filtrationThe solid (triphexylphosphine oxide) was filtered
  4. washrinsed with hexane
  5. customthe filtrate evaporated
  6. customto give crude product which
  7. distillationwas distilled at 0.5 mm Hg
  8. customthe fraction boiling at 130° C. was collected

出典と根拠

ORDレコード
ord-0e7189dc0bc449adae615e9a6618f4e8
出典データセット
uspto-grants-1993_12
特許番号
US05272145

関連ノート

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