Hydrochloric Acid → 4-(Benzyloxy)cyclohexanone

HRID 1631874Notes

Reaction equation

HRID 1631874 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:18][CH2:17][C:12]2(OCC[O:13]2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.O>[CH2:1]([O:8][CH:9]1[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 109873694-(Benzyloxy)cyclohexanoneYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

8-Benzyloxy-1,4-dioxa-spiro[4.5]decane (15 g, 60 mmol) was dissolved in THF (150 ml) and 1M aqueous hydrochloric acid (40 ml) is added and the reaction mixture is heated to reflux overnight. The reaction mixture is cooled and diluted with water (200 ml) before being extracted with ethyl acetate (1×200 ml). The organic extract is washed with saturated solution of sodium bicarbonate and then dried over magnesium sulphate, filtered and evaporated under reduced pressure to give an oil. The oil is distilled under vacuum in a kugelrohr to give 4-benzyloxy-cyclohexanone (10 g).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture is cooled
  4. extractionbefore being extracted with ethyl acetate (1×200 ml)
  5. extractionThe organic extract
  6. washis washed with saturated solution of sodium bicarbonate
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give an oil
  11. distillationThe oil is distilled under vacuum in a kugelrohr

Sources & evidence

ORD record
ord-2d4bdaf4e61849e1af21de6a7ba3911c
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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