Potassium Carbonate → Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoate

HRID 1249006Notes

Reaction equation

HRID 1249006 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][CH2:17][CH2:16][O:11][C:6]1[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 14330004Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoateYield 55.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.91 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 2.91 g of ethyl 4-bromobutyrate and 3.1 g of anhydrous potassium carbonate in 35 ml of anhydrous dimethyl formamide was stirred and heated at 75° for 12 hours. The solvent was removed in vacuo, the residue was treated with water and the product was extracted with ethyl acetate. The dried (over magnesium sulfate) extract was concentrated in vacuo and the crude product was purified by chromatography on 200 g of silica gel. Elution with 5% ethyl acetate-toluene gave 2.55 g (54% yield) of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoic acid ethyl ester, the titled compound, as an oil.

Workup

  1. temperatureheated at 75° for 12 hours
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with water
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe dried (over magnesium sulfate)
  6. extractionextract
  7. concentrationwas concentrated in vacuo
  8. customthe crude product was purified by chromatography on 200 g of silica gel
  9. washElution with 5% ethyl acetate-toluene

Sources & evidence

ORD record
ord-7db097c4e2d54afd9606995a964ccc7e
Source dataset
uspto-grants-1986_12
Patent number
US04628115

Reaction notes

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