Ethylene Glycol → 1-(4-CHLOROPHENYL)-4-OXOCYCLOHEXANECARBOXYLIc acid

HRID 1576205Notes

Reaction equation

HRID 1576205 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#N.[OH-:17].[K+].C(O)C[OH:21]>O>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)([OH:21])=[O:17]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 122302381-(4-Chlorophenyl)-4-oxocyclohexanecarbonitrile2×

Product 1

HCID 204534561-(4-CHLOROPHENYL)-4-OXOCYCLOHEXANECARBOXYLIc acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21.87 g. (0.079 mole) of 4-cyano-4-(4-chlorophenyl)cyclohexanone, ethylene ketal (prepared in Example 19) and 22 g. of potassium hydroxide in 220 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 is 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 19.26 g. (82.2% yield) of 4-carboxy-4-(4-chlorophenyl)cyclohexanone, ethylene ketal, having a melting point of 162.5° to 164.5°C.

Workup

  1. additionA mixture of 21.87 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 19.26 g

Sources & evidence

ORD record
ord-9e51990ebb644347a7484e0565a0feee
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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