Benzaldehyde → 7-Phenyl-6-heptenoic acid

HRID 2254348노트

반응식

HRID 2254348 반응식
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[CH:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[O-]CCCC.[K+]>C(O)(C)C>[C:30]1([CH:29]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 23699084Potassium butoxide

생성물 1

HCID 539006207-Phenyl-6-heptenoic acid수율 85.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

5-Carboxypentyl-triphenylphosphonium bromide (20 g) and benzaldehyde (5.6 g) were suspended in isopropanol (100 ml). To the suspension was added potassium butoxide (10.8 g) in limited amounts at 25° C., then the reaction was allowed to proceed for 2 hours at 70° C. Isopropanol was distilled off under reduced pressure. To the residue was added water (100 ml) to make a solution, which was acidified with hydrochloric acid, followed by extraction with ethyl acetate. The extract was washed with water, dried and concentrated under reduced pressure. The concentrate was subjected to a silica gel column chromatography to afford 7-phenyl-6-heptenoic acid (7.6 g) as a colorless oily product.

후처리

  1. distillationIsopropanol was distilled off under reduced pressure
  2. additionTo the residue was added water (100 ml)
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-af3be43a14534b888ad950dd8449731b
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05235091

반응 노트

불러오는 중…