Ethyl chloroacetate → (4-Acetyl-3-hydroxy-2-propylphenoxy)acetic acid

HRID 652501Notes

Reaction equation

HRID 652501 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].Cl[CH2:16][C:17]([O:19]CC)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:12]([C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:16][C:17]([OH:19])=[O:18])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13753869(4-Acetyl-3-hydroxy-2-propylphenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 24.25 g of 1-(2,4-dihydroxy-3-propylphenyl) ethanone, 16.0 ml of ethyl chloroacetate and 26 g of anhydrous potassium carbonate in 375 ml of anhydrous acetone was stirred at reflux for 17 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an oil which was crystallized from ethanol to give 27.2 g of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid, the titled compound, mp 61°-64°, (78% yield) in two crops.

Workup

  1. temperatureat reflux for 17 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to an oil which
  4. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-eb7738d70d664d1fad7aaab46bea972b
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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