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

HRID 327246

반응식

HRID 327246 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e7189dc0bc449adae615e9a6618f4e8
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272145

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