Sulfuric Acid → 2-tert-Butylcyclohexanone

HRID 434751Notes

Reaction equation

HRID 434751 reaction equation
[C:1]([C:5]1(O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:15].[Na+].[Na+].S(=O)(=O)(O)O>CCOCC.O>[C:1]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 108005Sodium dichromate dihydrateHCID 2879171-Tert-butylcyclohexan-1-ol

Product 1

HCID 1026812-tert-Butylcyclohexanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 31.25 g. (0.20 mole) t-butylcyclohexanol in 80 ml. of ethyl ether was cooled to 10° C. To this was added dropwise, with stirring, a solution of 21.0 g. (0.07 mole) sodium dichromate dihydrate and 15.75 ml. (0.30 mole) concentrated sulfuric acid in 100 ml. water while maintaining the reaction mixture below 25° C. The mixture was then warmed to room temperature, stirred for two hours, poured onto ice-water, ether layer separated, the aqueous phase extracted again with ether and the combined extracts washed with water, sodium bicarbonate and dried (MgSO4). Evaporation of the ether afforded 30.6 g. (99%) of the desired ketone.

Workup

  1. additionTo this was added dropwise
  2. stirringstirred for two hours
  3. customseparated
  4. extractionthe aqueous phase extracted again with ether
  5. washthe combined extracts washed with water, sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the ether
  8. customafforded 30.6 g

Sources & evidence

ORD record
ord-7bd598844ca24a16b2192ad16cb2f5e0
Source dataset
uspto-grants-1983_08
Patent number
US04399163

Reaction notes

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