Ethylene Glycol → Diisopropylether hexane

HRID 1762232Notes

Reaction equation

HRID 1762232 reaction equation
C(OC1[CH:14]=[C:13]([O:15][CH2:16][C:17]2C=CC=CC=2)[CH:12]=CC=1[C@H]1[C@H](CC=C)CCC(=O)C1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33](O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:16]([O:15][CH:13]([CH3:12])[CH3:14])([CH3:17])[CH3:33].[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 15670660HCID 15670660, compound

Product 1

HCID 21881879Diisopropylether hexane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.0 g. (11.73 mmole) of trans-3-(2,4-dibenzyloxyphenyl)-4-(2-propenyl)cyclohexanone, 6.5 ml. (117 mmole) of ethylene glycol and 223 mg. (1.17 mmole) of p-toluenesulfonic acid in 50 ml. of benzene was heated at reflux for 1.5 hours. Water was removed via a soxhlet extractor filled with molecular sieves. The reaction was cooled and added to 500 ml. saturated sodium bicarbonate and 300 ml. ether. The ether phase was separated, dried over magnesium sulfate and evaporated. Trituration with diisopropyl ether-hexane gave 5.31 g. (96%) of the title compound.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureat reflux for 1.5 hours
  3. customWater was removed via a soxhlet extractor
  4. additionfilled with molecular sieves
  5. temperatureThe reaction was cooled
  6. additionadded to 500 ml
  7. customThe ether phase was separated
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-d9baf52537fe4f659fd7b847d8b9dd7b
Source dataset
uspto-grants-1989_05
Patent number
US04831059

Reaction notes

Loading…