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

HRID 1600157Notes

Reaction equation

HRID 1600157 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-4one, 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-61ba38951cc24e1a976feddc9d2edfdd
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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