Hydrochloric Acid → 4-Hydroxy-3,3-dimethylcyclohexanone

HRID 1749387Notes

Reaction equation

HRID 1749387 reaction equation
[CH3:1][C:2]1([CH3:13])[CH:11]([OH:12])[CH2:10][CH2:9][C:4]2(OCC[O:5]2)[CH2:3]1.Cl.C(OCC)(=O)C>CO>[OH:12][CH:11]1[CH2:10][CH2:9][C:4](=[O:5])[CH2:3][C:2]1([CH3:13])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 90037844HCID 90037844, compound

Product 1

HCID 114992344-Hydroxy-3,3-dimethylcyclohexanoneYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7,7-dimethyl-1,4-dioxaspiro[4.5]decan-8-ol (1.0 equiv.) in 2.0 N hydrochloric acid aqueous solution (3.7 equiv.) and MeOH (0.9 M) was stirred at room temperature overnight. TLC (petroleum ether:ethyl acetate=3:1) showed that the reaction was completed. The solvent was removed under reduced pressure, the resulting residue was basified with saturated aqueous sodium bicarbonate solution and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to give 4-hydroxy-3,3-dimethylcyclohexanone (88% yield), which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ (ppm) 3.69-3.71 (m, 1H), 2.42-2.45 (m, 2H), 2.09-2.25 (m, 1H), 2.04-2.08 (m, 4H), 1.91-1.95 (m, 1H), 0.98 (s, 6H)

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-87525a5e108a4cab949c6bda158945b4
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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