Potassium Carbonate → Chromanone

HRID 1607445Notes

Reaction equation

HRID 1607445 reaction equation
C[C:2]1(C)[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6](O)=[CH:7][C:8]=2O)[O:3]1.C(=O)([O-])[O-].[K+].[K+].S(OC(CCCC1C=CC=CC=1)C)(=O)(=O)C>CN(C)C=O>[O:3]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[C:10](=[O:12])[CH2:11][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8213625,7-Dihydroxy-2,2-dimethylchroman-4-oneHCID 128783865-Phenyl-2-pentanol mesylate

Product 1

HCID 68110Chromanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,2-dimethyl-5,7-dihydroxy-4-chromanone (2.08 g, 10 mM), potassium carbonate (2.76 g, 20 mM), N,N-dimethylformamide (10 ml) and 5-phenyl-2-pentanol mesylate (2.64 g, 11 mM), under a nitrogen atmosphere, is heated to 80°-82° C. in an oil bath for 1.75 hours. The mixture is cooled to room temperature and then poured into ice/water (100 ml). The aqueous solution is extracted with ethyl acetate (2×25 ml) and the combined extracts washed successively with water (3×25 ml) and saturated brine (1×25 ml). The extract is then dried (MgSO4), decolorized with charcoal and evaporated to give the product as an oil which crystallizes upon seeding with pure product; m.p. 83°-84° C. Yield=quantitative.

Workup

  1. temperatureunder a nitrogen atmosphere, is heated to 80°-82° C. in an oil bath for 1.75 hours
  2. extractionThe aqueous solution is extracted with ethyl acetate (2×25 ml)
  3. washthe combined extracts washed successively with water (3×25 ml) and saturated brine (1×25 ml)
  4. dry with materialThe extract is then dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-6f949981046c4a6fadd9dfd5c5d9807a
Source dataset
uspto-grants-1989_09
Patent number
US04863934

Reaction notes

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