Nitric Acid → 2,2,6-Trimethylcyclohexanecarboxylic acid

HRID 1975640

Reaktionsgleichung

Reaktionsgleichung von HRID 1975640
[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].C1(C)C=CC=CC=1>O>[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]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 1140TolueneHCID 103695Cyclohexanecarboxaldehyde, 2,2,6-trimethyl-

Produkt 1

HCID 142287142,2,6-Trimethylcyclohexanecarboxylic acidAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

In a 300-ml 4-necked flask equipped with a condenser, a thermometer, a dropping funnel, and a stirrer was placed 40 g of nitric acid (60% aqueous solution) and heated to 55° C. To the solution was added dropwise 95 g (0.62 mole) of 2,2,6-trimethylcyclohexanecarbaldehyde (4) composed of 90% of the trans-form and 10% of the cis-form synthesized in Synthesis Example 2-A) described above over a period of 2 hours. Thereafter, the reaction was carried out for 3 hours at the same temperature. Then, 100 g of toluene and 100 g of water were added to the reaction mixture at room temperature to wash with water and form an organic layer and an aqueous layer separately. The organic layer was washed thrice with 100 g of a saturated aqueous sodium chloride solution, and 80 ml of the toluene was distilled off under reduced pressure by means of an evaporator, to provide 104 g of crude 2,2,6-trimethylcyclohexanecarboxylic acid (5) composed of 89% of the trans-form and 11% of the cis-form (boiling point: 44° to 54° C.). The mass spectra of the cis- and trans-forms of the acid (5) were the same as those in Synthesis Example 1.

Aufarbeitung

  1. customIn a 300-ml 4-necked flask equipped with a condenser
  2. customsynthesized in Synthesis Example 2-A)
  3. customdescribed above over a period of 2 hours
  4. washto wash with water
  5. customform an organic layer
  6. washThe organic layer was washed thrice with 100 g of a saturated aqueous sodium chloride solution, and 80 ml of the toluene
  7. distillationwas distilled off under reduced pressure by means of an evaporator

Quellen und Nachweise

ORD-Eintrag
ord-b6a01990cb8546d196964cf84a46e09f
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288702

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