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

HRID 2164923Notes

Reaction equation

HRID 2164923 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 32.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 15.0 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 15.0 g of ethyl 4-bromobutyrate, 16.0 g of anhydrous potassium carbonate in 200 ml of anhydrous dimethylformamide was stirred and heated at 75° for 24 hours. The solvent was removed in vacuo and the residue was purified by high pressure liquid chromatography using 2.5% ethyl acetate-toluene to yield 7.62 g of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoic acid ethyl ester as an oil.

Workup

  1. temperatureheated at 75° for 24 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-b8d42834aaa34a0f9b34c4c81a84a2be
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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