Potassium Hydroxide → HCID 65425682, compound

HRID 1045055Notes

Reaction equation

HRID 1045055 reaction equation
C[O:2][C:3]([C:5]1([CH2:14][CH3:15])[CH2:10][CH2:9][CH:8]([CH:11]([CH3:13])[CH3:12])[CH2:7][CH2:6]1)=[O:4].[OH-].[K+]>CCO>[CH2:14]([C:5]1([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][CH:8]([CH:11]([CH3:13])[CH3:12])[CH2:9][CH2:10]1)[CH3:15]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67044939HCID 67044939, compound

Product 1

HCID 65425682HCID 65425682, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Isopropyl-cyclohexanecarboxylic acid methyl ester (1.1 g, 6 mmol) was alkylated using a method analogous to General Procedure F using LDA (9 mmol) and iodoethane (1.4 g, 9 mmol) in THF (20 mL) at −78° C. to RT to produce 1-ethyl-4-isopropyl-cyclohexanecarboxylic acid methyl ester (1.0 g, 78% yield) as a mixture of isomers. Hydrolysis of this ester using KOH (12.5 mmol) in aqueous EtOH (1:1; 5 mL) at 150° C. for 2 hr in a pressurized vessel following a microwave method analogous to General Procedure G2 gave 1-ethyl-4-isopropyl-cyclohexanecarboxylic acid (800 mg, 86% yield) as a mixture of isomers after workup by evaporation of the solvent, treatment with aq 2 N HCl, extractive workup, and evaporation of the solvent.

Workup

  1. additionas a mixture of isomers
  2. customat 150° C.
  3. customfor 2 hr

Sources & evidence

ORD record
ord-2dc915d9c4c14fd49b49f97019f77833
Source dataset
uspto-grants-2013_10
Patent number
US08563742B2

Reaction notes

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