Methanol → 3-Methoxy-4-methylcinnamic acid

HRID 1436000ノート

反応式

HRID 1436000 の反応式
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]

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 542687393-(3-Methoxy-4-methyl-phenyl)acrylic acid methyl ester

生成物 1

HCID 534017143-Methoxy-4-methylcinnamic acid収率 93.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. additionwater added
  3. filtrationThe mixture was filtered
  4. addition5 M HCl was added until precipitation
  5. filtrationThe mixture was filtered
  6. washthe solid precipitate washed with water
  7. customdried in-vacuo

出典と根拠

ORDレコード
ord-048a51cd80b3476e9b17606f06caff77
出典データセット
uspto-grants-2009_11
特許番号
US07618985B2

反応ノート

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