2-Methylbenzaldehyde → HCID 53820978, compound

HRID 704399Notes

Reaction equation

HRID 704399 reaction equation
[C:1]1([CH3:9])[C:2]([CH:7]=O)=[CH:3][CH:4]=[CH:5][CH:6]=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>O1CCCC1>[CH3:9][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:29][C:30]([O:32][CH3:33])=[O:31]

Participants

4

Reactant 2

HCID 107222-MethylbenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 53820978HCID 53820978, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.20 g of o-tolualdehyde in 20 ml of anhydrous tetrahydrofuran was added to a suspension of 3.67 g of methyl (triphenylphosphoranylidene)acetate in 20 ml of anhydrous tetrahydrofuran at room temperature, and the mixture was refluxed for 15 hours. The solvent was then distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography (40 g). Elution with hexane-ethyl acetate (2:1) gave 1.65 g of methyl 2-methylcinnamate.

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. washElution with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-3efa940524b446ae82c4af9b4035d097
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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