4-Methylcyclohexanone → 6-Bromo-4'-methylspiro(chroman-2,1'-cyclohexan)-4-one

HRID 1408682Notes

Reaction equation

HRID 1408682 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:12][CH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:16]1([CH2:17][CH2:18][CH:13]([CH3:12])[CH2:14][CH2:15]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 115254-MethylcyclohexanoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 584240346-Bromo-4'-methylspiro(chroman-2,1'-cyclohexan)-4-oneYield 156.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (20 g, 0.093 mol), 4-methylcyclohexanone (21.31 g, 0.187 mol) and pyrrolidine (12.63 g, 0.178 mol) in methanol (400 mL) was refluxed for overnight. The reaction mixture was concentrated in vacuo, diluted with an equal volume of H2O and then added HCl until pH=1. The resulting mixture was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromo-4′-methylspiro(chroman-2,1′-cyclohexan)-4-one (45 g, 100%).

Workup

  1. temperaturewas refluxed for overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with an equal volume of H2O
  4. extractionThe resulting mixture was extracted with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a507d3fd2ed142aebdd4c7b56d6c9d5b
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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