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

HRID 2240770노트

반응식

HRID 2240770 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-91ee5d7f34f1404d8635836de98546e0
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723378B2

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