Ethyl chloroacetate → Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate

HRID 1249002Notes

Reaction equation

HRID 1249002 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][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[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])[CH3:21]

Participants

5

Reactant 3

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

Product 1

HCID 13389144Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate

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 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 ethyl ester, 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-2c47e4fa4e6b4abe96ea9ebd5f42c5a6
Source dataset
uspto-grants-1986_12
Patent number
US04628115

Reaction notes

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