HCID 54073385, compound → HCID 57254550, compound

HRID 377151Notes

Reaction equation

HRID 377151 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([C@H:16]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][CH2:18][C@@H:17]1[OH:24])[CH3:15]>CC(C)=O>[CH2:14]([C@H:16]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][CH2:18][C:17]1=[O:24])[CH3:15]

Participants

4

Reactant 2

HCID 54073385HCID 54073385, compoundHCID 131709961Jones' reagent

Product 1

HCID 57254550HCID 57254550, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.8 ml of Jones' reagent (2.5 M, 7.0 mmol), prepared according to Fieser, vol. 1, p. 142 (CrO3 +H2SO4 +H2O) were added dropwise to a stirred solution of (+)-(1S,2S)-2-ethyl-4,4-dimethyl-1-cyclohexanol (1.09 g, 7.0 mmol) in acetone (70 ml) at 5°. The temperature rose to 7°, and a green suspension was formed. Stirring was continued for 10 min, the reaction mixture was then poured on a mixture of ice/NaCl/pentane, extracted with pentane, washed, dried, concentrated, and the crude product (1.40 g) was distilled in a bulb-to-bulb apparatus (oven 70°, 3 Torr). 1.01 g of (+)-(2S)-2-ethyl-4,4-dimethyl-1-cyclohexanone were obtained (yield 91%).

Workup

  1. customrose to 7°
  2. customa green suspension was formed
  3. extractionextracted with pentane
  4. washwashed
  5. customdried
  6. concentrationconcentrated
  7. distillationthe crude product (1.40 g) was distilled in a bulb-to-bulb apparatus (oven 70°, 3 Torr)

Sources & evidence

ORD record
ord-30145e26899b41d09c9e8a3449aac8be
Source dataset
uspto-grants-2000_02
Patent number
US06025323

Reaction notes

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