Hydrochloric Acid → 4-(Benzyloxy)cyclohexanone

HRID 1970981Notes

Reaction equation

HRID 1970981 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CC(C)=O.CCOC(C)=O>[CH2:1]([O:8][CH:9]1[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 109873694-(Benzyloxy)cyclohexanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 8-(benzyloxy)-1,4-dioxaspiro[4.5]decane (12 g, 48.3 mmol) in acetone was added HCl (2 M, 50 mL, 100 mmol). The reaction mixture was heated to 50° C. overnight, cooled to room temperature, diluted with EtOAc, and washed with water and sodium bicarbonate solution. The organic layer was dried, and concentrated to give the title compound. 1H NMR (600 MHz, CDCl3) δ 7.25-7.36 (m, 5H); 4.58 (s, 2H); 3.81 (m, 1H); 2.60 (m, 2H); 2.25 (m, 2H); 2.13 (m, 2H); 1.94 (m, 2H).

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water and sodium bicarbonate solution
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8c8eb30833504f8cbec502c5396be21d
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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