Ethylene Glycol → 1-(3,4-Dimethoxyphenyl)-4-oxocyclohexanecarboxylic Acid

HRID 1576208Notes

Reaction equation

HRID 1576208 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#N.[OH-:20].[K+].C(O)C[OH:24]>O>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)([OH:24])=[O:20]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 749913Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-

Product 1

HCID 204533371-(3,4-Dimethoxyphenyl)-4-oxocyclohexanecarboxylic AcidYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17.54 g. (0.058 mole) of 4-cyano-4-(3,4-dimethoxy)cyclohexanone, ethylene ketal (prepared as in Example 22) and 17.5 g. of potassium hydroxide in 175 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 19 g. (99% yield) of 4-carboxy-4-(3,4-dimethoxyphenyl)cyclohexanone, ethylene ketal, as an amorphous gum.

Workup

  1. additionA mixture of 17.54 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 19 g

Sources & evidence

ORD record
ord-611f0231e4c54c6a9af51dfce489e350
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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