Methanol → 3-Methoxy-4-methylcinnamic acid

HRID 1436000Notes

Reaction equation

C[O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([O:13][CH3:14])[CH:7]=1.[OH-].[Na+].O.CO>O1CCCC1>[CH3:14][O:13][C:8]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]([OH:15])=[O:2])[CH:11]=[CH:10][C:9]=1[CH3:12]

Participants

Conditions

Temperature: 50 °C

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-methoxy4-methyl-phenyl)acrylic acid methyl ester (27 g, 0.126 mol). A mixture of 3-(3-methoxy4-methyl-phenyl)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

concentrationThe mixture was concentrated in vacuo
additionwater added
filtrationThe mixture was filtered
addition5 M HCl was added until precipitation
filtrationThe mixture was filtered
washthe solid precipitate washed with water
customdried in-vacuo

Sources & evidence

ORD record: ord-048a51cd80b3476e9b17606f06caff77
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618985B2

Reaction notes

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