8-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane → Cyclohexanone, 4-[(phenylmethoxy)methyl]-

HRID 1401757Notes

Reaction equation

HRID 1401757 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:19][CH2:18][C:13]2(OCC[O:14]2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:11][CH2:12][C:13](=[O:14])[CH2:18][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 103780318-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 10443381Cyclohexanone, 4-[(phenylmethoxy)methyl]-Yield 89%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5.0 g (19.1 mmol) of 8-(benzyloxymethyl)-1,4-dioxaspiro[4,5]decane was dissolved in 150 ml of 1N aqueous hydrochloric acid solution, and the solution was stirred at room temperature for one hour. The reaction solution was washed twice with 100 ml of chloroform and neutralized with sodium carbonate. The neutralized solution was extracted twice with 100 ml of ethyl acetate and the organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain 4-(benzyloxymethyl)cyclohexanone (3.7 g, 89%) as a pale yellow oil.

Workup

  1. washThe reaction solution was washed twice with 100 ml of chloroform and neutralized with sodium carbonate
  2. extractionThe neutralized solution was extracted twice with 100 ml of ethyl acetate
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4242f5e176474614b845ebf8412d2522
Source dataset
uspto-grants-2014_12
Patent number
US08907128B2

Reaction notes

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