Potassium Hydroxide → 1-(3,4-Dimethoxyphenyl)-4-oxocyclohexanecarboxylic Acid

HRID 462281Notes

Reaction equation

HRID 462281 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.ClC1C=CC(C2(C#N)CCC(=[O:33])CC2)=CC=1.[OH-:36].[K+]>C(O)CO>[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:33])=[O:36]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 749913Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-HCID 122302381-(4-Chlorophenyl)-4-oxocyclohexanecarbonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Following the procedure of Example 1, Part E, but substituting 17.54 gm. (0.058 mole) of 4-cyano-4-(3,4-dimethoxyphenyl)cyclohexanone, ethylene ketal (prepared in Part D, above) for the 21.87 gm. of 4-(p-chlorophenyl)-4-cyanocyclohexanone, ethylene ketal; and using 17.5 gm. (0.31 mole) potassium hydroxide and 175 ml. ethylene glycol instead of the 22.0 gm. and 220 ml., respectively; there is obtained, after removal of the ether, 19.0 gm. (99% yield) of 4-carboxy-4-(3,4-dimethoxyphenyl)cyclohexanone, ethylene ketal as a gum that gives a reasonably expected infrared spectrum.

Workup

  1. customthere is obtained
  2. customafter removal of the ether, 19.0 gm

Sources & evidence

ORD record
ord-1e701dddfd38469ca996b46e3adac3c1
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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