3-Methylbenzaldehyde → Methyl 3-(3-methylphenyl)prop-2-enoate

HRID 615507Notes

Reaction equation

HRID 615507 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.C1(P(=[CH:29][C:30]([O:32][CH3:33])=[O:31])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:9][C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[CH:7]=[CH:29][C:30]([O:32][CH3:33])=[O:31]

Participants

4

Reactant 2

HCID 121053-MethylbenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 20785957Methyl 3-(3-methylphenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.0 g (49.9 mmol) of m-tolualdehyde and 18.37 g (54.93 mmol) of methyl (triphenylphosphoranylidene)acetate in 50 ml of THF was stirred at reflux for 4 hours. The THF was evaporated and the residue was stirred with 200 ml of petroleum ether (bp=30°-60° C.) and filtered. The filtrate was evaporated to give the title compound as a light yellow liquid which was distilled bulb-to-bulb at 90° C./0.4 mm of Hg.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe THF was evaporated
  3. stirringthe residue was stirred with 200 ml of petroleum ether (bp=30°-60° C.)
  4. filtrationfiltered
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-efcea47e59ad4d1c980e2355e312bc08
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

Loading…