Acetone → Methyl 2,2-dimethyl-4-oxochroman-6-carboxylate

HRID 402794Notes

Reaction equation

HRID 402794 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[CH3:15][C:16]([CH3:18])=O.N1CCCC1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:15][C:16]1([CH3:18])[CH2:2][C:1](=[O:3])[C:4]2[C:13](=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=2)[O:14]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 12332833Methyl 3-acetyl-4-hydroxybenzoate

Product 1

HCID 14608497Methyl 2,2-dimethyl-4-oxochroman-6-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-acetyl-4-hydroxybenzoate (200 mg, 1.03 mmol), acetone (151 μL, 2.06 mmol) and pyrrolidine (25.6 μL, 0.31 mmol) were mixed in toluene (515 μL) and stirred at room temperature for 1 hour. It was then heated to 100° C. for 5 hours, allowed to cool to room temperature, diluted with EtOAc (50.0 mL) and poured into ice. The two layers were separated. The organic layer was washed with 2 N aqueous HCl (10.0 mL), 2 N aqueous NaOH (10.0 mL), water (10.0 mL), dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-30% EtOAc/hexanes to give the desired product as a pale-yellow oil.

Workup

  1. temperatureIt was then heated to 100° C. for 5 hours
  2. temperatureto cool to room temperature
  3. additionpoured into ice
  4. customThe two layers were separated
  5. washThe organic layer was washed with 2 N aqueous HCl (10.0 mL), 2 N aqueous NaOH (10.0 mL), water (10.0 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude mixture was purified by silica gel chromatography
  10. washeluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-cadd41fd442245b680a3e74cca31c196
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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