Hydrochloric Acid → HCID 22467169, compound

HRID 1934763Notes

Reaction equation

HRID 1934763 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([OH:21])[CH2:20][CH2:19][C:14]3(OCC[O:15]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.O.C(OCC)(=O)C>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([OH:21])[CH2:12][CH2:13][C:14](=[O:15])[CH2:19][CH2:20]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 8857Ethyl AcetateHCID 22467107HCID 22467107, compound

Product 1

HCID 22467169HCID 22467169, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran was dissolved 1.10 g of 8-[4-(tert-butyl)phenyl]-1,4-dioxaspiro[4.5]decane-8-ol. Then, 5.00 ml of 6 mol/L hydrochloric acid and 5.00 ml of water were added at an ice-cooled temperature and the resulting mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into a mixture of water and ethyl acetate, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was added to the residue, and the resulting crystal was collected by filtration to obtain 0.67 g of 4-[4-(tert-butyl)phenyl]-4-hydroxy-1-cyclohexanone as a colorless crystalline product.

Workup

  1. temperaturecooled temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was added to the residue
  7. filtrationthe resulting crystal was collected by filtration

Sources & evidence

ORD record
ord-443f9347dbbd4ffa883db3033e186a3d
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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