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

HRID 2231441Notes

Reaction equation

HRID 2231441 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[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 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenone

Product 1

HCID 13389144Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetateYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.88 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 2.4 ml of ethyl bromoacetate and 4.0 g of anhydrous potassium carbonate in 50 ml of anhydrous acetone was stirred at reflux for 6 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an oil which was purified by chromatography on silica gel. Elution with 20% ethyl acetate-toluene gave 4.13 g, mp 51°-52°, (73% yield) of (4acetyl-3-hydroxy-2-propylphenoxy)acetic acid ethyl ester.

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to an oil which
  4. customwas purified by chromatography on silica gel
  5. washElution with 20% ethyl acetate-toluene

Sources & evidence

ORD record
ord-9a3a4add5f464c2b957420271cdbcc94
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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