(3,6-Dimethyl-1,2-phenylene)dimethanol → 4,7-Dimethyl-3H-isobenzofuran-1-one

HRID 1879525노트

반응식

HRID 1879525 반응식
[OH:1][CH2:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([CH3:10])[C:4]=1[CH2:11][OH:12]>[O-2].[Mn+4].[O-2].ClCCl>[CH3:9][C:8]1[CH:7]=[CH:6][C:5]([CH3:10])=[C:4]2[C:3]=1[CH2:2][O:1][C:11]2=[O:12]

참가 물질

4

반응물 1

HCID 13220177(3,6-Dimethyl-1,2-phenylene)dimethanol

생성물 1

HCID 5839124,7-Dimethyl-3H-isobenzofuran-1-one수율 92%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

A 1 L 3-necked RBF is charged with 1,2-bis(hydroxymethyl)-3,6-dimethyl-benzene 3 (22.05 g, 0.133 mol), activated 85% manganese(IV) oxide (135.69 g, 1.327 mol), 4 Å molecular sieves (12.00 g) and anhydrous dichloromethane (500 mL), and placed under nitrogen. The reaction mixture is heated to reflux and stirred for 22 h. The reaction mixture is filtered through Kieselguhr and washed thoroughly with dichloromethane. The filtrate is concentrated in vacuo to yield the product 4 as a cream solid (19.79 g, 92%): 1H-NMR (300 MHz, CDCl3) δ 7.31 (d, 1H, 3J=7.5 Hz), 7.18 (d, 1H, 3J=7.5 Hz), 5.18 (s, 2H), 2.65 (s, 3H), 2.29 (s, 3H); 13C-NMR (75 MHz, CDCl3) δ 171.7, 145.8, 136.9, 134.5, 130.8, 129.3, 122.9, 68.3, 16.96, 16.91.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. filtrationThe reaction mixture is filtered through Kieselguhr
  4. washwashed thoroughly with dichloromethane
  5. concentrationThe filtrate is concentrated in vacuo

출처 및 근거

ORD 기록
ord-e7245aecc2e24e989bb4edf0e5e8c72e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318048B2

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