Acetone → 4-(2-Hydroxy-2-methylpropoxy)-4-methylcyclohexanone

HRID 1688732Notes

Reaction equation

HRID 1688732 reaction equation
[CH3:1][C:2]([OH:17])([CH3:16])[CH2:3][O:4][C:5]1([CH3:15])[CH2:14][CH2:13][C:8]2(OCC[O:9]2)[CH2:7][CH2:6]1.Cl.CC(C)=O>O>[OH:17][C:2]([CH3:16])([CH3:1])[CH2:3][O:4][C:5]1([CH3:15])[CH2:14][CH2:13][C:8](=[O:9])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 670097012-Methyl-1-[(8-methyl-1,4-dioxaspiro[4.5]dec-8-yl)oxy]propan-2-ol

Product 1

HCID 670098904-(2-Hydroxy-2-methylpropoxy)-4-methylcyclohexanoneYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methyl-1-[(8-methyl-1,4-dioxaspiro[4.5]dec-8-yl)oxy]propan-2-ol (1.81 g), 3N hydrochloric acid (20 mL) and acetone (20 mL) was stirred at room temperature for 18 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→65/35 (volume ratio)] to give the title compound as a colorless oil (1.05 g, 71%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=80/20→65/35 (volume ratio)]

Sources & evidence

ORD record
ord-8896e7f6e42245d28940b376f63dc408
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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