Sulfuric Acid → 4-(4-Fluorophenyl)cyclohexan-1-one

HRID 12052Notes

Reaction equation

HRID 12052 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 128344048-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 128343224-(4-Fluorophenyl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

8-(4-fluor-phenyl)-1,4-dioxaspiro[4.5]decane (2 mmol) is dissolved in dioxane (6.5 ml) and treated with 3 ml 50% aqueous sulphuric acid accompanied by stirring at room temperature for 5 hours. After dilution with water (12 ml) extraction is carried out twice with dichloromethane. The raw title compound is obtained from the combined organic phases after drying over sodium sulphate and evaporating-off of the solvent in a vacuum (Tetrahedron 1998, 54, 15509-15524): tR 3.44 min (LC-1); ESI-MS(+): m/z 193.29 [M+H]+.

Workup

  1. extractionAfter dilution with water (12 ml) extraction

Sources & evidence

ORD record
ord-078b576691f14997974b7557469bacb0
Source dataset
uspto-grants-2010_06
Patent number
US07727979B2

Reaction notes

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