Nitric Acid → 2,2,6-Trimethylcyclohexanecarboxylic acid

HRID 1975643

Reaction equation

HRID 1975643 reaction equation
[N+]([O-])(O)=[O:2].[CH3:5][C:6]1([CH3:15])[CH2:11][CH2:10][CH2:9][CH:8]([CH3:12])[CH:7]1[CH:13]=[O:14]>>[CH3:15][C:6]1([CH3:5])[CH2:11][CH2:10][CH2:9][CH:8]([CH3:12])[CH:7]1[C:13]([OH:2])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 103695Cyclohexanecarboxaldehyde, 2,2,6-trimethyl-

Product 1

HCID 142287142,2,6-Trimethylcyclohexanecarboxylic acidYield 98.9%

Conditions

Temperature
55 °C

Procedure

In a 300-ml 4-necked flask equipped with a condenser, a thermometer, a dropping funnel, and a stirrer was placed 39 g of nitric acid (aqueous 60% solution), and the temperature was raised to 55° C. Then, 93 g (0.60 mole) of 2,2,6-trimethylcyclohexanecarbaldehyde [composition: 90.2% of the trans-form, 9.8% of the cis-form] synthesized in Synthesis Example 6-A) was added dropwise thereto over a period of 2 hours. Thereafter, the reaction was carried out for 3 hours at the same temperature, and the reaction mixture obtained was washed with of 100 g of toluene and 100 g of water, followed by separating an organic layer from an aqueous layer. After further washing thrice the organic layer with 100 g of a saturated aqueous sodium chloride solution, the organic layer formed was separated from an aqueous layer. The toluene was distilled off from the organic layer by an evaporator under reduced pressure to provide 101 g of crude 2,2,6-trimethylcyclohexanecarboxylic acid (5) [composition: 90.5% of the trans-form, 9.5% of the cis-form].

Workup

  1. customIn a 300-ml 4-necked flask equipped with a condenser
  2. additionwas added dropwise
  3. waitThereafter, the reaction was carried out for 3 hours at the same temperature
  4. customthe reaction mixture obtained
  5. washwas washed with of 100 g of toluene and 100 g of water
  6. customby separating an organic layer from an aqueous layer
  7. washAfter further washing thrice the organic layer with 100 g of a saturated aqueous sodium chloride solution
  8. customthe organic layer formed
  9. customwas separated from an aqueous layer
  10. distillationThe toluene was distilled off from the organic layer by an evaporator under reduced pressure

Sources & evidence

ORD record
ord-244e7457554a449a9afc0ff4b6f7cdfd
Source dataset
uspto-grants-1994_02
Patent number
US05288702

Linked notes

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