2',4'-Dihydroxyacetophenone → HCID 21460859, compound

HRID 1959139Notes

Reaction equation

HRID 1959139 reaction equation
N1CCCC1.[CH3:6][CH2:7][C:8](=O)[CH2:9][CH3:10].[OH:12][C:13]1[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=1[C:20](=[O:22])[CH3:21]>CO>[CH2:7]([C:8]1([CH2:9][CH3:10])[CH2:21][C:20](=[O:22])[C:14]2[C:13](=[CH:18][C:17]([OH:19])=[CH:16][CH:15]=2)[O:12]1)[CH3:6]

Participants

5

Reactant 3

HCID 69902',4'-DihydroxyacetophenoneHCID 7288Ethyl ketoneHCID 31268Pyrrolidine

Product 1

HCID 21460859HCID 21460859, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyrrolidine (9.3 g) and pentan-3-one (11.3 g) were added to a solution of 1-(2,4-dihydroxyphenyl)ethanone (14 g) in methanol (150 mL) and the solution was stirred for 24 hours and then heated under reflux for 10 hours. The reaction mixture was concentrated in vacuo, and to the residue was added water (10 mL). To the mixture was added 1N hydrochloric acid solution to adjust its pH to 5 to 6, and extracted with ethyl acetate (25 mL×3). The combined organic layer was dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The resultant crude product was purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=10/1) to give the titled compound (8 g) as a colorless powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 10 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionto the residue was added water (10 mL)
  5. additionTo the mixture was added 1N hydrochloric acid solution
  6. extractionextracted with ethyl acetate (25 mL×3)
  7. dry with materialThe combined organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe resultant crude product was purified by column chromatography on silica gel (Solvent; petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-0ee303a1b50a487f92f602301a67c1d2
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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