Benzaldehyde → 7-Phenyl-6-heptenoic acid

HRID 2254348Notes

Reaction equation

HRID 2254348 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 539006207-Phenyl-6-heptenoic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-af3be43a14534b888ad950dd8449731b
Source dataset
uspto-grants-1993_08
Patent number
US05235091

Reaction notes

Loading…