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

HRID 1437489Notes

Reaction equation

HRID 1437489 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), 2NNaOH (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), 2NNaOH (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-69a4093882a146f5ae73e5f47aafd4dc
Source dataset
uspto-grants-2009_11
Patent number
US07622493B2

Reaction notes

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