Hydrochloric Acid → 4-(Benzyloxy)cyclohexanone

HRID 1349381Notes

Reaction equation

HRID 1349381 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.O.[Cl-].[Na+]>C(OC(C)C)(C)C>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 5234Sodium ChlorideHCID 111394858-(Benzyloxy)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 109873694-(Benzyloxy)cyclohexanoneYield 95.5%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

294 g of 8-benzyloxy-1,4-dioxaspiro[4.5]decane were dissolved in 1400 ml of diisopropyl ether, and 580 ml of four molar hydrochloric acid were added. After 20 hours' stirring at room temperature, 300 ml of water and 180 ml of saturated sodium chloride solution were added, and stirring was carried out for a further four hours. The phases were separated, and the aqueous phase was neutralized with solid sodium hydrogen carbonate and extracted repeatedly with diisopropyl ether. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Distillation under a high vacuum yielded 231 g of 4-benzyloxycyclohexanone.

Workup

  1. stirringstirring
  2. waitwas carried out for a further four hours
  3. customThe phases were separated
  4. extractionextracted repeatedly with diisopropyl ether
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. distillationDistillation under a high vacuum

Sources & evidence

ORD record
ord-7ed9ad444b05461b8a4d88bd1d148764
Source dataset
uspto-grants-2007_05
Patent number
US07211694B2

Reaction notes

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