Hydrochloric Acid → Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylphenoxyacetate

HRID 615495Notes

Reaction equation

HRID 615495 reaction equation
[CH3:1][CH2:2][CH2:3][C:4]1[C:9]([OH:10])=[C:8]([C:11]([CH3:13])=[O:12])[CH:7]=[CH:6][C:5]=1[OH:14].Br[CH2:16][C:17]1[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].Cl>CC(C)=O.O>[C:11]([C:8]1[CH:7]=[CH:6][C:5]([O:14][CH2:16][C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=2)=[C:4]([CH2:3][CH2:2][CH3:1])[C:9]=1[OH:10])(=[O:12])[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 12870369Ethyl 2-[4-(bromomethyl)phenoxy]acetate

Product 1

HCID 53927753Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)methylphenoxyacetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 1 g (5.15 mmoles) of 2,4-dihydroxy-3-propylacetophenone and 2.0 g (5.15 mmoles) of ethyl 4-bromomethylphenoxyacetate in 50 ml of dry acetone was stirred and refluxed with 800 mg of K2CO3 for 48 hours. The reaction mixture was diluted with H2O, rendered acidic with 6N HCl and extracted into CH2Cl2. Evaporation of the CH2Cl2 gave an oil that was chromatographed on silica gel by gradient elution with 50% CH2Cl2 /hexane to 75% CH2Cl2 /hexane to provide the title compound as a white solid.

Workup

  1. extractionextracted into CH2Cl2
  2. customEvaporation of the CH2Cl2
  3. customgave an oil that
  4. customwas chromatographed on silica gel by gradient elution with 50% CH2Cl2 /hexane to 75% CH2Cl2 /hexane

Sources & evidence

ORD record
ord-82860dbb6f134c2b851eba325ce6a2ff
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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