3-Methoxybenzaldehyde → 2-Propenal, 3-(3-methoxyphenyl)-, (2E)-

HRID 1602569Notes

Reaction equation

HRID 1602569 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[CH:11]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12]>C1(C)C=CC=CC=1>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[CH:1]=[CH:13][CH:11]=[O:12]

Participants

4

Reactant 2

HCID 115693-MethoxybenzaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde

Product 1

HCID 5956962-Propenal, 3-(3-methoxyphenyl)-, (2E)-Yield 24.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

680 mg of m-anisaldehyde and 1.52 g of formylmethylenetriphenylphosphorane were dissolved in 10 ml of toluene and stirred under heating at 120 ° C. for 7 hours. The reaction solution was cooled to room temperature and purified by silica gel column chromatography [hexane/ethyl acetate=9/1→4/1] to give 199 mg of the title compound as a yellow oily substance.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. custompurified by silica gel column chromatography [hexane/ethyl acetate=9/1→4/1]

Sources & evidence

ORD record
ord-c06d09cc80ca4539b29589dc248677d9
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

Loading…