Ethylene Glycol → 1,4-Dioxa-8-thiaspiro(4.5)decane

HRID 1290447Notes

Reaction equation

HRID 1290447 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH2:8](O)[CH2:9][OH:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[O:10]1[C:4]2([CH2:5][CH2:6][S:1][CH2:2][CH2:3]2)[O:7][CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 123359781,4-Dioxa-8-thiaspiro(4.5)decane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g of tetrahydrothiopyran-4-one, 2.5 ml of ethylene glycol, 0.230 g of p-toluenesulfonic acid and 125 ml of benzene is stirred at reflux temperature for 2.5 hours. The water formed is removed using a Dean-Stark trap. The reaction is treated with saturated sodium bicarbonate, water, saturated sodium chloride, dried and concentrated in vacuo to give 6.52 g of the desired product as an oil.

Workup

  1. temperatureat reflux temperature for 2.5 hours
  2. customis removed
  3. additionThe reaction is treated with saturated sodium bicarbonate, water, saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2538209aee874718ae07da6b8842ca51
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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