Sulfuric Acid → 4β-tert-Butylcyclohexane-1α-carboxylic acid methyl ester

HRID 1527610Notes

Reaction equation

HRID 1527610 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:21]O>CO>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH3:21])=[O:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 1367594-Tert-butylcyclohexane-1-carboxylic acidHCID 23721981Sodium hydroxide methanol

Product 1

HCID 5303054β-tert-Butylcyclohexane-1α-carboxylic acid methyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 630 g of methanol was dissolved 203 g of 4-tert-butylcyclohexanecarboxylic acid. The solution was combined with 0.54 g of conc. sulfuric acid and heated under reflux for 72 hours. The reaction solution was allowed to cool to room temperature, 18 g of 2.5 wt % sodium hydroxide/methanol mixture was added, and the solvent was distilled off in vacuum from the reaction solution. The crude oil was purified by vacuum distillation, obtaining 207 g of methyl 4-tert-butylcyclohexanecarboxylate as colorless liquid (yield 95%, isomer ratio 76:24).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 72 hours
  3. distillationthe solvent was distilled off in vacuum from the reaction solution
  4. distillationThe crude oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-fab4bf0704f0436ea3d4e09c1c9c94ac
Source dataset
uspto-grants-2015_07
Patent number
US09086624B2

Reaction notes

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