Cyclohexanone → Spiro[chroman-2,1'-cyclohexan]-4-one

HRID 1908690Notes

Reaction equation

HRID 1908690 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.N1CCCC1>C1(C)C=CC=CC=1.CCOCC>[C:11]12([CH2:9][C:8](=[O:10])[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:1]1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 83752'-HydroxyacetophenoneHCID 31268Pyrrolidine

Product 1

HCID 11106781Spiro[chroman-2,1'-cyclohexan]-4-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2′-hydroxyacetophenone (Aldrich, CAS#118-93-4, 2.72 g, 20 mmol), cyclohexanone (2.7 mL, 26.1 mmol), and pyrrolidine (1.66 mL, 19.9 mmol) was stirred in 6 mL toluene at room temperature for 1 h and at reflux (Dean-Stark trap) for 4 h. After cooling to room temperature, the mixture was diluted with ether (30 mL), washed sequentially with 2N HCl (10 mL), 2N NaOH (10 mL), and H2O (10 mL), dried over Na2SO4, and filtered. Evaporation of volatiles in vacuo afforded the crude title compound, which was used without further purification.

Workup

  1. temperatureat reflux (Dean-Stark trap) for 4 h
  2. washwashed sequentially with 2N HCl (10 mL), 2N NaOH (10 mL), and H2O (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customEvaporation of volatiles in vacuo

Sources & evidence

ORD record
ord-c68412f1bb5a4e7d920548113922ea4d
Source dataset
uspto-grants-2013_12
Patent number
US08598220B2

Reaction notes

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