Ethylene Glycol → 1-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid

HRID 1576206Notes

Reaction equation

HRID 1576206 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([F: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]([F: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 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile

Product 1

HCID 219553321-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18.17 g. (0.07 mole) of 4-cyano-4-(4-fluorophenyl)cyclohexanone, ethylene ketal (prepared in Example 20 and 15 g. of potassium hydroxide in 150 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 to give 18.2 g. (93% yield) of 4-carboxy-4-(4-fluorophenyl)cyclohexanone, ethylene ketal, having a melting point of 117° to 122°C.

Workup

  1. additionA mixture of 18.17 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. customto give 18.2 g

Sources & evidence

ORD record
ord-fc7c456a4a014edbb3844c4bdd824d1b
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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