3-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid → 3-(4-Formyl-2,6-dimethyl-phenyl)-propionic acid

HRID 1665908ノート

反応式

HRID 1665908 の反応式
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:5]([CH3:15])[CH:4]=1>C(O)(=O)C.O=[Mn]=O>[CH:2]([C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:5]([CH3:15])[CH:4]=1)=[O:1]

参加物

4

反応物 1

HCID 574374033-(4-Hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid

生成物 1

HCID 574374043-(4-Formyl-2,6-dimethyl-phenyl)-propionic acid収率 84.3%

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-(4-hydroxymethyl-2,6-dimethyl-phenyl)-propionic acid (960 mg, 4.6 mmol) in acetic acid (20 mL), MnO2 (1440 mg, 16.6 mmol) is added. The mixture is stirred at 80° C. for 4.5 h before it is filtered. The filtrate is evaporated and the crude product is purified by CC on silica gel eluting with DCM containing 8% of methanol to give 3-(4-formyl-2,6-dimethyl-phenyl)-propionic acid (800 mg) as a beige solid; LC-MS: tR=0.81 min; 1H NMR (D6-DMSO): δ 12.2 (s br, 1H), 9.86 (s, 1H), 7.52 (s, 2H), 2.93-2.85 (m, 2H), 2.38-2.30 (m, 8H).

後処理

  1. filtrationis filtered
  2. customThe filtrate is evaporated
  3. customthe crude product is purified by CC on silica gel eluting with DCM containing 8% of methanol

出典と根拠

ORDレコード
ord-87aa9d5368d84544b7ccae9d4074988d
出典データセット
uspto-grants-2011_10
特許番号
US08039644B2

反応ノート

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