Acetone → HCID 15043720, compound

HRID 1655367Notes

Reaction equation

HRID 1655367 reaction equation
O[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:12][C:13]([CH3:15])=[O:14].N1CCCC1>C1(C)C=CC=CC=1>[CH3:12][C:13]1([CH3:15])[CH:2]([CH3:11])[C:3](=[O:4])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:14]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 1011212-Hydroxy-1-phenyl-1-propanone

Product 1

HCID 15043720HCID 15043720, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-hydroxypropiophenone (500 ml, 3.64 mol), acetone (400 ml), and pyrrolidine (150 ml, 1.8 mol) in toluene (1000 ml) was heated at 85° C. for 66 hours. The cooled solution was then washed successively with water, aqueous hydrochloric acid and aqueous sodium hydroxide solution. The toluene layer was separated and the solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/heptane (50/50), to give 81 g of 2,2,3-trimethyl-3,4-dihydro-2H-1-benzopyran-4-one as an oil, a compound of formula (3 a) ; 1H NMR (CDCl3): δ 1.3 (d, 3H) , 1.4 (s,3H), 1.6 (s,3H), 2.5-3.0 (q,1H), 6.8-8.1 (m,4H).

Workup

  1. washThe cooled solution was then washed successively with water, aqueous hydrochloric acid and aqueous sodium hydroxide solution
  2. customThe toluene layer was separated
  3. customthe solvent removed under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. washeluting with dichloromethane/heptane (50/50)

Sources & evidence

ORD record
ord-cd4b374899184d60a02c487607543b8a
Source dataset
uspto-grants-1993_10
Patent number
US05250547

Reaction notes

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