8-(2-Chlorophenylmethyl)-1,4-dioxaspiro[4.5]decane → 4-(2-Chlorophenylmethyl)cyclohexanone

HRID 1735294Notes

Reaction equation

HRID 1735294 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1>O.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 197052768-(2-Chlorophenylmethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 197052324-(2-Chlorophenylmethyl)cyclohexanoneYield 77.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4.8 grams (0.018 mole) of 8-(2-chlorophenylmethyl)-1,4-dioxaspiro[4.5]decane in 25 mL of water and 100 mL of acetic acid was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was carefully partitioned between diethyl ether and an aqueous solution saturated with sodium bicarbonate. The combined ether extracts were then washed with an aqueous solution saturated with sodium chloride. The organic layer was then dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 3.1 grams of 4-(2-chlorophenylmethyl)cyclohexanone, mp 48° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customAfter this time the reaction mixture was carefully partitioned between diethyl ether
  2. washThe combined ether extracts were then washed with an aqueous solution saturated with sodium chloride
  3. dry with materialThe organic layer was then dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-07b7efdb39f04556ab237e98803646a2
Source dataset
uspto-grants-1996_07
Patent number
US05536725

Reaction notes

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