2-Chlorobenzaldehyde → 2-Chlorocinnamaldehyde

HRID 743402Notes

Reaction equation

HRID 743402 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=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:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:29][CH:30]=[O:31]

Participants

4

Reactant 2

HCID 69962-ChlorobenzaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde

Product 1

HCID 30140422-ChlorocinnamaldehydeYield 68.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following a procedure similar to that described in the first part of Preparation 17, 3.00 g of 2-chlorobenzaldehyde and 7.5 g of (triphenylphosphoranylidene)acetaldehyde were reacted in 100 ml of acetonitrile. The crude product thus obtained 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 2.44 g (yield 68%) of 3-(2-chlorophenyl)-2-propenal as a solid.

Workup

  1. customThe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3ec02909709d487c874bb027c60589aa
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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