Methanol → 3-Methoxy-4-methylcinnamic acid

HRID 1366749노트

반응식

HRID 1366749 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 534017143-Methoxy-4-methylcinnamic acid수율 93.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4bf4c1b69a034ee78404d03f905869c0
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893088B2

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