Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(3-Methoxy-4-methyl-phenyl)acrylic acid methyl ester

HRID 1366748Notes

Reaction equation

HRID 1366748 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH3:11])[CH:6]=O.[C:12]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH3:15])=[O:13]>C1(C)C=CC=CC=1>[CH3:15][O:14][C:12](=[O:13])[CH:16]=[CH:6][C:5]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 47150953-Methoxy-4-methylbenzaldehyde

Product 1

HCID 542687393-(3-Methoxy-4-methyl-phenyl)acrylic acid methyl esterYield 97.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-methoxy-4-methylbenzaldehyde (19.3 g, 0.129 mol), carbomethoxy methylene triphenylphosphorane (51 g) in toluene (250 ml) was refluxed for 24 h. The mixture was quenched with aqueous ammonium chloride and extracted with ethyl acetate and concentrated in vacuo to give a residue. The residue was purified by flash chromatography using ethyl acetate-heptane (1:1) to give 3-(3-methoxy-4-methyl-phenyl)acrylic acid methyl ester (27 g, 0.126 mol). A mixture of 3-(3-methoxy-4-methylphenyl)acrylic acid methyl ester (27 g), sodium hydroxide (14 g), water (70 ml), methanol (140 ml) and tetrahydrofuran (70 ml) was refluxed at 50° C. for 1 h. The mixture was concentrated in vacuo and then water added. The mixture was filtered and 5 M HCl was added until precipitation occurred. The mixture was filtered and the solid precipitate washed with water and dried in-vacuo to give 3-(3-methoxy-4-methylphenyl)acrylic acid (23.5 g, 0.122 mol).

Workup

  1. temperaturewas refluxed for 24 h
  2. customThe mixture was quenched with aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-33ba7d212a2949e99e528d568e373e11
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

Loading…