2',4'-Dihydroxyacetophenone → HCID 15171688, compound

HRID 1681120Notes

Reaction equation

HRID 1681120 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)C.[C:12]([O-])(=O)C.[Na+].[C:17](=[O:20])(O)[O-].[Na+].[CH3:22][CH2:23][CH2:24][CH2:25]CC.[C:28]([O:31][CH2:32][CH3:33])(=[O:30])[CH3:29]>C(OC(=O)CC)(=O)CC>[CH2:5]([C:6]1[O:8][C:23]2[CH:22]=[C:32]([O:31][C:28](=[O:30])[CH2:29][CH3:12])[CH:33]=[CH:25][C:24]=2[C:17](=[O:20])[C:7]=1[C:2](=[O:1])[CH2:3][CH3:9])[CH3:4]

Participants

6

Reactant 4

HCID 69902',4'-DihydroxyacetophenoneHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 21226206Ethyl acetate hexane

Product 1

HCID 15171688HCID 15171688, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 31263Propionic anhydrideSolvent

Procedure

A solution of 5 g (32.2.10-3 mol) of 1-(2,4-dihydroxyphenyl)ethanone and 4 g (48.8.10-3 mol) of sodium acetate in 40 ml of propionic anhydride is kept at a temperature of 170° C. under an inert atmosphere for 20 hours. The reaction mixture is hydrolyzed in the presence of sodium bicarbonate and the product is extracted with ethyl acetate and then washed with water. The organic phase obtained is dried over magnesium sulfate. The solvent is evaporated off under reduced pressure. After the addition of toluene, the remaining solvents are evaporated off again under reduced pressure. After purification by chromatography on silica gel using a hexane/ethyl acetate mixture (6/1 v/v) as the eluent, 2 g (yield: 20%) of the expected product are obtained.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. washwashed with water
  3. customThe organic phase obtained
  4. dry with materialis dried over magnesium sulfate
  5. customThe solvent is evaporated off under reduced pressure
  6. additionAfter the addition of toluene
  7. customthe remaining solvents are evaporated off again under reduced pressure

Sources & evidence

ORD record
ord-68c2001d0eed4923963acb284cd84ce4
Source dataset
uspto-grants-1992_12
Patent number
US05169838

Reaction notes

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