Hydrochloric Acid → 4-Hydroxy-4-methylcyclohexanone

HRID 1500885Notes

Reaction equation

HRID 1500885 reaction equation
[CH3:1][C:2]1([OH:12])[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[CH2:4][CH2:3]1.Cl.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[OH:12][C:2]1([CH3:1])[CH2:11][CH2:10][C:5](=[O:6])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 187130758-Methyl-1,4-dioxaspiro(4.5)decan-8-ol

Product 1

HCID 285394-Hydroxy-4-methylcyclohexanoneYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-methyl-1,4-dioxaspiro[4.5]decan-8-ol (6.1 g, 35.5 mmol) in THF (200 mL) was added 2 N HCl (32 mL). The resulting mixture was stirred at RT overnight, and then was basified to pH 8.0 by saturated K2CO3 solution. The separated organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel (EA:PE=3:20 to 2:3) to afford the title compound as yellow oil (4.1 g, yield: 86.7%).

Workup

  1. concentrationThe separated organic layer was concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel (EA:PE=3:20 to 2:3)

Sources & evidence

ORD record
ord-cfc4b1bd013c48528d9a7ad2a6893a5c
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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