p-Toluenesulfonic acid → 2-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-2-yl)ethanol

HRID 23755

反応式

HRID 23755 の反応式
[CH2:1]([O:4][C:5]1[C:9]([O:10][CH2:11][CH2:12][CH3:13])=[CH:8][S:7][CH:6]=1)CC.C(O)C(O)CC[OH:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[O:10]1[CH:11]([CH2:12][CH2:13][OH:18])[CH2:1][O:4][C:5]2=[CH:6][S:7][CH:8]=[C:9]12

参加物

4

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 183021,2,4-ButanetriolHCID 114013973,4-Di-n-propoxythiophene

生成物 1

HCID 225903432-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-2-yl)ethanol

実験手順

9.06 g (45.2 mmol) of 3,4-di-n-propoxythiophene, 24.0 g (226 mmol) of 1,2,4-butanetriol and 0.09 g (0.5 mmol) of p-toluenesulphonic acid were heated to 150 to 160° C. (bath temperature) under N2 for 2 h. During this time, 5.89 g of distillate (substantially n-propanol) were collected. The cooled liquid was diluted with 50 ml of methylene chloride, washed to neutrality with water and the organic phase was dried over Na2SO4. After filtering and evaporating the methylene chloride at 1 mbar, distillation was then effected. According to 1H NMR spectroscopy, the fraction collected between 45 and 128° C. (1.63 g=19.4% of overall theoretical yield of transetherification products) consisted of approx. 81.5% of 2-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)ethanol, 6.5% of 3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepin-2-ylmethanol and 12% of 2,3,4,5-tetrahydrothieno[3,4-b][1,4]dioxocin-3-ol.

後処理

  1. distillationDuring this time, 5.89 g of distillate (substantially n-propanol) were collected
  2. additionThe cooled liquid was diluted with 50 ml of methylene chloride
  3. washwashed
  4. dry with materialthe organic phase was dried over Na2SO4
  5. filtrationAfter filtering
  6. customevaporating the methylene chloride
  7. distillationat 1 mbar, distillation
  8. customthe fraction collected between 45 and 128° C. (1.63 g=19.4% of overall theoretical yield of transetherification products)

出典と根拠

ORDレコード
ord-c9f796b4cb3744f2a7cdc4743b550efd
出典データセット
uspto-grants-2005_02
特許番号
US06852831B2

関連ノート

読み込み中…