3-Chlorobenzaldehyde → 3-(3-Chlorophenyl)prop-2-enal

HRID 743398Notes

Reaction equation

HRID 743398 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C1(P(=[CH:29][CH:30]=[O:31])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:29][CH:30]=[O:31])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 114773-ChlorobenzaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde

Product 1

HCID 27631113-(3-Chlorophenyl)prop-2-enalYield 59.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.00 g of 3-chlorobenzaldehyde and 6.49 g of (triphenylphosphoranylidene)acetaldehyde in 100 ml of acetonitrile was heated under reflux for 5 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 2.11 g (yield 59%) of 3-(3-chlorophenyl)-2-propenal as a solid.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-fd4d15d613ac4722b99327433968d852
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

Loading…