Ethylparaben → 4-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethoxy]-benzoic acid ethyl ester

HRID 652525Notes

Reaction equation

HRID 652525 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[C:7]([OH:14])[C:6]=1[CH2:15][CH2:16][CH3:17].[CH2:18]([O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[CH2:18]([O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[C:7]([OH:14])[C:6]=2[CH2:15][CH2:16][CH3:17])=[CH:24][CH:23]=1)[CH3:19]

Participants

6

Reactant 3

HCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 138819842-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethyl bromide

Product 1

HCID 139128244-[2-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethoxy]-benzoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g of 1-[4-(2-bromoethoxy)-2-hydroxy-3- propylphenyl]ethanone 0.83 g of 4-hydroxybenzoic acid ethyl ester and 0.95 g of anhydrous potassium carbonate in 30 ml of anhydrous acetone and 10 ml of anhydrous DMF was stirred at reflux for 20 hours. The mixture was filtered and solvent was removed in vacuo. The residue was dissolved in ethyl acetic and washed with water. The extract was dried over magnesium sulfate) and concentrated in vacuo to an oil which was purified by HPLC using 25% ethyl acetate-hexane to give 1.3 g, m.p. 99-100 (75%) of 4-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]-benzoic acid ethyl ester, the title compound. Analysis Calculated for C22H26O6 : C, 68.36; H, 6.78. Found: C, 68.39; H, 6.79.

Workup

  1. temperatureat reflux for 20 hours
  2. filtrationThe mixture was filtered
  3. customsolvent was removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetic
  5. washwashed with water
  6. dry with materialThe extract was dried over magnesium sulfate) and
  7. concentrationconcentrated in vacuo to an oil which
  8. customwas purified by HPLC

Sources & evidence

ORD record
ord-c9b3213683214731bfa9aad9f415fe15
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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