Ethylene Glycol → 4-Oxo-1-phenylcyclohexane-1-carboxylic acid

HRID 1955281Notes

Reaction equation

HRID 1955281 reaction equation
C(C1(C2C=CC=CC=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#N.C1(C)C=CC(S(O)(=O)=[O:23])=CC=1.[CH2:27]([OH:30])[CH2:28]O.[C:31]1(C)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[C:31]1([C:28]2([C:27]([OH:30])=[O:23])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 912824-Oxo-1-phenylcyclohexanenitrile

Product 1

HCID 3438864-Oxo-1-phenylcyclohexane-1-carboxylic acidYield 81%

Procedure

4-Cyano-4-phenylcyclohexanone (25 mmol) was refluxed for 2 h with p-toluenesulfonic acid (2.5 mmol) and ethyleneglycol (30 mmol) in toluene (150 mL) using a Dean-Stark trap. The reaction mixture was partitioned between Et2O and 2 M NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The resulting oil was refluxed with KOH (40%, 200 mL) in ethyleneglycol (120 mL) for 3 h. Conc. HCl was added and the mixture was allowed to cool. It was than extracted with Et2O, dried (Na2SO4) and evaporated affording 4.4 g (81%) of the desired compound; 1H NMR (CDCl3) δ 2.2-2.5 (m, 4H), 2.55 (m, 2H), 2.74 (m, 2H), 7.25-7.50 (m, 5H), 8.0 (br, 1H).

Workup

  1. customThe reaction mixture was partitioned between Et2O and 2 M NaHCO3
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. temperatureThe resulting oil was refluxed with KOH (40%, 200 mL) in ethyleneglycol (120 mL) for 3 h
  5. additionConc. HCl was added
  6. temperatureto cool
  7. extractionthan extracted with Et2O
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-4b8390108469494894882ef50aa0a79b
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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