p-Toluenesulfonic acid → HCID 22590342, compound

HRID 23756

Reaction equation

HRID 23756 reaction equation
[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[CH2:18][CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[O:10]1[CH:11]([CH2:12][CH2:13][CH2:18][CH2:19][OH:20])[CH2:1][O:4][C:5]2=[CH:6][S:7][CH:8]=[C:9]12

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 78231,2,6-HexanetriolHCID 114013973,4-Di-n-propoxythiophene

Product 1

HCID 22590342HCID 22590342, compound

Procedure

9.06 g (45.2 mmol) of 3,4-di-n-propoxythiophene, 30.3 g (226 mmol) of 1,2,6-hexanetriol and 0.09 g (0.5 mmol) of p-toluenesulphonic acid are heated to 150 to 165° C. (bath temperature) under N2 for 3 h. During this time, 5.8 g of distillate (substantially n-propanol) were collected. The cooled liquid was diluted with 50 ml of methylene chloride, washed to neutrality and to free it of hexanetriol with water and the organic phase was dried over Na2SO4. After filtering and evaporating the methylene chloride, the residue (6.73 g=74.8% of theory) was identified by 1H NMR spectroscopy (in CDCl3 against TMS) using δ=6.30 ppm (2H, thiophene H) and 2.85 ppm (1H, OH) as being substantially 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)-1-butanol.

Workup

  1. distillationDuring this time, 5.8 g of distillate (substantially n-propanol) were collected
  2. additionThe cooled liquid was diluted with 50 ml of methylene chloride
  3. washwashed to neutrality
  4. dry with materialthe organic phase was dried over Na2SO4
  5. filtrationAfter filtering
  6. customevaporating the methylene chloride

Sources & evidence

ORD record
ord-d92287d6b2ae41aa84fbe9104e260357
Source dataset
uspto-grants-2005_02
Patent number
US06852831B2

Linked notes

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