Hydrochloric Acid → 4-Hydroxy-4-methylcyclohexanone

HRID 509282Notes

Reaction equation

HRID 509282 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>C1COCC1>[OH:12][C:2]1([CH3:1])[CH2:11][CH2:10][C:5](=[O:6])[CH2:4][CH2:3]1

Participants

4

Reactant 2

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

Product 1

HCID 285394-Hydroxy-4-methylcyclohexanoneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-Methyl-1,4-dioxaspiro[4.5]decane-8-ol (650 mg, 3.77 mmol) was dissolved in THF (10 ml), followed by addition of 1N aqueous HCl solution (5 ml), and then the resulting mixture was stirred at room temperature for 6 hours. The resulting reaction liquid was concentrated under reduced pressure, and then extracted with 10% MeOH/MC (20 ml×5). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (50% EtOAc/Hexanes), to obtain 443 mg of yellow oil (92%).

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. extractionextracted with 10% MeOH/MC (20 ml×5)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfollowed by filtration and concentration
  6. customthe residue thus obtained

Sources & evidence

ORD record
ord-4c8d104f2237465ead45294b8349f757
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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