Nitric Acid → HCID 15764988, compound

HRID 1975642Notes

Reaction equation

HRID 1975642 reaction equation
[N+]([O-])(O)=[O:2].[CH3:5][C:6]1([CH3:15])[CH2:11][CH2:10][CH2:9][C@@H:8]([CH3:12])[C@@H:7]1[CH:13]=[O:14]>>[CH3:15][C:6]1([CH3:5])[CH2:11][CH2:10][CH2:9][C@@H:8]([CH3:12])[C@@H:7]1[C:13]([OH:2])=[O:14]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 12132910(1S,6R)-2,2,6-Trimethylcyclohexanecarboxaldehyde

Product 1

HCID 15764988HCID 15764988, compoundYield 98.7%

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 38 g of nitric acid (aqueous 60% solution) and heated to 55° C. Then, 90 g of (1S,6R)-2,2,6-trimethylcyclohexanecarbaldehyde (14) [composition: 91% of the (1S,6R)-form, 9% of the (1R,6R)-form] synthesized in Synthesis Example 5-A) was added dropwise thereto with stirring over a period of 2 hours. After carrying out the reaction for 3 hours at the same temperature, the reaction mixture was washed with water with 90 g of toluene and 100 g of water at room temperature, followed by separating an organic layer formed from an aqueous layer. The organic layer was washed thrice with 100 g of a saturated aqueous sodium chloride solution, followed by separating the organic layer from an aqueous layer. The toluene was distilled off from an organic layer by an evaporator under reduced pressure to provide 98 g of crude (1S,6R)-2,2,6-trimethylcyclohexanecarboxylic acid (15) [composition: 91% of the (1S,6R)-form, 9% of the (1R,6R)-form]. The product was recrystallized from methylene chloride as a solvent to provide 46 g of pure (1S,6R)-2,2,6-trimethylcyclohexanecarboxylic acid (15) [melting point: 67° C. to 68° C.; optical rotation; [α]D25 =-14.40°].

Workup

  1. customIn a 300-ml 4-necked flask equipped with a condenser
  2. additionwas added dropwise
  3. customthe reaction for 3 hours at the same temperature
  4. washthe reaction mixture was washed with water with 90 g of toluene and 100 g of water at room temperature
  5. customby separating an organic layer
  6. customformed from an aqueous layer
  7. washThe organic layer was washed thrice with 100 g of a saturated aqueous sodium chloride solution
  8. customby separating the organic layer from an aqueous layer
  9. distillationThe toluene was distilled off from an organic layer by an evaporator under reduced pressure

Sources & evidence

ORD record
ord-5d05e5bb1a5041d39e08fef165b253e4
Source dataset
uspto-grants-1994_02
Patent number
US05288702

Reaction notes

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