Ethylene Glycol → 1-(4-Methoxyphenyl)-4-oxocyclohexanecarboxylic Acid

HRID 1576207Notes

Reaction equation

HRID 1576207 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([C:18]#N)([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3]C1.[OH-:21].[K+].C(O)C[OH:25]>O>[C:18]([C:7]1([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]1)([OH:25])=[O:21]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 122302431,4-Dioxaspiro[4.5]decane-8-carbonitrile, 8-(4-methoxyphenyl)-

Product 1

HCID 215147791-(4-Methoxyphenyl)-4-oxocyclohexanecarboxylic AcidYield 83.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 27.98 g. (0.103 mole) of 4-cyano-4-(4-methoxyphenyl)cyclohexanone ethylene ketal (prepared in Example 21) and 28 g. of potassium hydroxide in 280 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 methylene chloride and Skellysolve B to give 22.35 g. (83.1% yield) of 4-carboxy-4-(4-methoxyphenyl)cyclohexanone, ethylene ketal, having a melting point of 154° to 155.5°C.

Workup

  1. additionA mixture of 27.98 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 methylene chloride and Skellysolve B
  8. customto give 22.35 g

Sources & evidence

ORD record
ord-18cd73fd84b7441980edc888b4f01a17
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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