8-Phenoxy-1,4-dioxaspiro[4.5]decane → 4-Phenoxycyclohexanone

HRID 2099618Notes

Reaction equation

HRID 2099618 reaction equation
[O:1]([CH:8]1[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.Cl>[O:1]([CH:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 189804238-Phenoxy-1,4-dioxaspiro[4.5]decane

Product 1

HCID 224671324-PhenoxycyclohexanoneYield 56%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of compound 8-phenoxy-1,4-dioxa-spiro[4.5]decane (2.0 g, 8.55 mmol) in THF (12 mL), 3N HCl (aqueous, 12 mL) was added and the reaction mixture was stirred at 50° C. for 3 h. Excess THF was removed in rotary evaporator and the crude reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:4) to obtain 4-phenoxy-cyclohexanone (900 mg, 56%) as a white solid.

Workup

  1. customExcess THF was removed in rotary evaporator
  2. customthe crude reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e615f981d0ef44de8ac7400efca5f219
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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