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

HRID 1879525ノート

反応式

HRID 1879525 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e7245aecc2e24e989bb4edf0e5e8c72e
出典データセット
uspto-grants-2012_11
特許番号
US08318048B2

反応ノート

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