(Triphenylphosphoranylidene)acetaldehyde → 5-Cyano-2-hydroxycinnamaldehyde

HRID 1268211Notes

Reaction equation

HRID 1268211 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH:10]=1)[CH:8]=O)#[N:2].C1(P(=[CH:31][CH:32]=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH:10]=1)[CH:8]=[CH:31][CH:32]=[O:33])#[N:2]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 117893503-Formyl-4-hydroxybenzonitrile

Product 1

HCID 734500315-Cyano-2-hydroxycinnamaldehydeYield 45.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-cyano-2-hydroxybenzaldehyde (4.3 g) and (triphenylphosphoranylidene)acetaldehyde (9.4 g) in toluene (150 ml) was stirred at 70° C. for 2 hours. The reaction mixture was concentrated in vacuo. The residue was purified by chromatography on a silica gel column using dichloromethane/ethyl acetate=3/1 as an eluant to give the desired compound (2.3 g, yield 44%) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-3c161023d2404210953f6fb78d03a8cd
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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