Ethylene Glycol → HCID 54050571, compound

HRID 648780Notes

Reaction equation

HRID 648780 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)CO.O>C1C=CC=CC=1>[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 174Ethylene Glycol2×HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 57008816HCID 57008816, compound

Product 1

HCID 54050571HCID 54050571, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of ethyl (4-keto-2-phenyl cyclohex-2-enyl)acetate (12.91 g.), p-toluene sulphonic acid monohydrate (0.95 g.) and ethylene glycol (2.93 ml.) in benzene (258 ml.) was heated under reflux using a Dean and Stark water separator for 2.5 hours. A further aliquot of ethylene glycol (0.7 ml.) was then added and the mixture heated under reflux for a further 3 hours. The reaction mixture was then cooled and the benzene evaporated. The residual mixture was dissolved in ether (500 ml.). The solution was extracted with saturated sodium bicarbonate solution (2×100 ml.). The combined extracts were washed with water (2×100 ml.), dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica, eluting with ether/hexane (3:1 v/v), to give the ethylene ketal of ethyl (4-keto-2-phenylcyclohex-1-enyl)acetate (9.35 g.) NMR (90 MHz): 1.20 (3H,t), 1.88 (2H,t). 2.38 (2H,t), 2.9 (2H,s), 4.0 (4H,s), 4.1 (2H,q) and 7.1-7.4 (5H,)ppm.

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture heated
  3. temperatureunder reflux for a further 3 hours
  4. temperatureThe reaction mixture was then cooled
  5. customthe benzene evaporated
  6. dissolutionThe residual mixture was dissolved in ether (500 ml.)
  7. extractionThe solution was extracted with saturated sodium bicarbonate solution (2×100 ml.)
  8. washThe combined extracts were washed with water (2×100 ml.)
  9. dry with materialdried (MgSO4)
  10. customevaporated under reduced pressure
  11. customThe crude product was purified by flash chromatography on silica
  12. washeluting with ether/hexane (3:1 v/v)

Sources & evidence

ORD record
ord-641ee649ecf745b7991ba1c64329807e
Source dataset
uspto-grants-1988_04
Patent number
US04736057

Reaction notes

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