Isopropanol → Cyclohexanone, 2,6-dimethyl-4-(3-methylbutyl)-

HRID 435207Notes

Reaction equation

HRID 435207 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][CH:15]1[CH2:20][CH:19]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:18][CH:17]([CH3:26])[CH:16]1[OH:27].C(O)(C)C>CC(C)=O>[CH3:14][CH:15]1[CH2:20][CH:19]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:18][CH:17]([CH3:26])[C:16]1=[O:27]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 20491271Cyclohexanol, 2,6-dimethyl-4-(3-methylbutyl)-HCID 131709961Jones' reagent2×

Product 1

HCID 20491278Cyclohexanone, 2,6-dimethyl-4-(3-methylbutyl)-Yield 72.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent (150 mL) was added dropwise at room temperature to a solution of 2,6-dimethyl-4-(3-methylbutyl)cyclohexanol (100 g. 0.5 mol, produced according to Example 4) in acetone (3,000 mL). The reaction mixture was stirred for 1 h and isopropanol added to decompose excess Jones reagent. The salts were removed by filtration and the solution concentrated on a rotary evaporator. The residue was taken up in ethyl acetate and washed successively with water (400 mL), 5% sodium bicarbonate (200 mL) and brine (200 mL). The organic layer was dried, the solvent evaporated, and the residue fractionated to yield 71 g of the ketone, bp 96°-100° C. (3 mm). NMR (CDCl3) δ0.8-1.1 (12H, m), 1.1-3.2 (12H, m). IR (film) 1725, 1140, 990 cm-1. MS (m/e) 196 (M+), 69, 82, 97, 41.

Workup

  1. customThe salts were removed by filtration
  2. concentrationthe solution concentrated on a rotary evaporator
  3. washwashed successively with water (400 mL), 5% sodium bicarbonate (200 mL) and brine (200 mL)
  4. customThe organic layer was dried
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-239690e22c874d31846d0bed53ddc4c4
Source dataset
uspto-grants-1983_08
Patent number
US04400545

Reaction notes

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