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

HRID 1576204Notes

Reaction equation

HRID 1576204 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#N.[OH-:16].[K+].C(O)C[OH:20]>O>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)([OH:20])=[O:16]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 912824-Oxo-1-phenylcyclohexanenitrile2×

Product 1

HCID 3438864-Oxo-1-phenylcyclohexane-1-carboxylic acidYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.27 g. (0.046 mole) of 4-cyano-4-phenylcyclohexanone, ethylene ketal (prepared in Example 18) and 11.3 g. of potassium hydroxide in 90 ml. of ethylene glycol is heated at reflux for about 16 hours. The resulting solution is allowed to cool, diluted with water and washed with ether. The aqueous layer was covered with ether and then cautiously acidified. The aqueous layer is extracted with two additional portions of ether and the extracts combined. The extracts are evaporated to dryness and the solid remaining is recrystallized from a mixture of ethylene chloride and Skellysolve B to give 10.51 g. (86.3% yield) of 4-carboxy-4-phenylcyclohexanone, ethylene ketal, having a melting point of 136° to 140°C.

Workup

  1. additionA mixture of 11.27 g
  2. temperatureat reflux for about 16 hours
  3. temperatureto cool
  4. washwashed with ether
  5. extractionThe aqueous layer is extracted with two additional portions of ether
  6. customThe extracts are evaporated to dryness
  7. customthe solid remaining is recrystallized from a mixture of ethylene chloride and Skellysolve B
  8. customto give 10.51 g

Sources & evidence

ORD record
ord-afe2894a90754c63b0bc85ff93abdbf2
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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