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

HRID 1694445Notes

Reaction equation

HRID 1694445 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-228f2a1704914021a58544fb64b8066b
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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