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

HRID 1688728Notes

Reaction equation

HRID 1688728 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14])[CH2:7][CH2:6]2)[O:4]CC1.Cl.CC(C)=O>O>[OH:15][C:13]([CH3:16])([CH3:14])[CH2:12][O:11][CH:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 670091781-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-methylpropan-2-ol

Product 1

HCID 670089144-(2-Hydroxy-2-methylpropoxy)cyclohexanoneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(1,4-dioxaspiro[4.5]dec-8-yloxy)-2-methylpropan-2-ol (5.53 g), 3N hydrochloric acid (30 mL) and acetone (30 mL) was stirred at room temperature for 16 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→60/40 (volume ratio)] to give the title compound as a colorless oil (3.25 g, 73%).

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→60/40 (volume ratio)]

Sources & evidence

ORD record
ord-31ed946d7dbc47e3b3b0068e81af2f92
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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