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

HRID 2164927Notes

Reaction equation

HRID 2164927 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[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[CH: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])[CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 14330021Ethyl 2-(4-acetyl-3-hydroxy-2-propylphenoxy)propanoateYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 10.0 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 8.4 ml of ethyl 2-bromopropionate and 10.7 g of anhydrous potassium carbonate in 125 ml of anhydrous acetone was stirred at reflux for 42 hours. The reaction mixture was filtered and the filtrate was concentrated to an oil which was purified by high pressure liquid chromatography using 2% ethyl acetate-toluene to yield 11.4 g (73%) of racemic-(4-acetyl-3-hydroxy-2-propylphenoxy)-alpha-methylacetic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 42 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to an oil which
  4. customwas purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-8a2260e58d8342a2b3e286ec5c3008d4
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

Loading…