Hydrochloric Acid → 4-(2-Benzyloxyethyl)cyclohexanone

HRID 1404399Notes

Reaction equation

HRID 1404399 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:20][CH2:19][C:14]2(OCC[O:15]2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(#N)C>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 218796038-[2-(Benzyloxy)ethyl]-1,4-dioxaspiro[4.5]decane

Product 1

HCID 218796054-(2-Benzyloxyethyl)cyclohexanoneYield 95.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 8-(2-(benzyloxy)ethyl)-1,4-dioxaspiro[4.5]decane (2.30 g, 8.32 mmol) in acetonitrile (18 mL) was added 6N HCl solution and the resulting solution was stirred at rt for 2 h. After removal of acetonitrile by evaporation, the residue was neutralized by solid NaHCO3, extracted with EtOAc, dried over Na2SO4. Filtration and evaporation to dryness gave the ketone as white solid (1.84 g, 95.5%).

Workup

  1. customAfter removal of acetonitrile
  2. customby evaporation
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation to dryness

Sources & evidence

ORD record
ord-f2e1ecd807d14a29a5790f184d016126
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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