p-Toluenesulfonic acid → HCID 22590343, 화합물

HRID 23755

반응식

HRID 23755 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

HCID 22590343HCID 22590343, 화합물

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c9f796b4cb3744f2a7cdc4743b550efd
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852831B2

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