1,3-Dibromopropane → 4-Acetyl-3-(3-bromopropoxy)-2-propylphenoxy acetic acid ethyl ester

HRID 2231442Notes

Reaction equation

HRID 2231442 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([OH:16])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2].[Br:21][CH2:22][CH2:23][CH2:24]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([O:16][CH2:24][CH2:23][CH2:22][Br:21])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate3×HCID 13389144Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate

Product 1

HCID 133891464-Acetyl-3-(3-bromopropoxy)-2-propylphenoxy acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.13 g of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid ethyl ester, 7.6 ml of 1,3-dibromopropane and 3.0 g of anhydrous potassium carbonate in 100 ml of anhydrous acetone was stirred at reflux for 73 hours. An additional 1.0 g of potassium carbonate was added and reflux was continued for 19 hours at which time 1.0 g of potassium carbonate was added. After 16 hours reflux, the reaction mixture was filtered and the filtrate was concentrated in vacuo. The crude product was chromatographed on 200 g of silica gel and eluted with 15% ethyl acetate-toluene to give 4.82 g of [4-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]acetic acid ethyl ester.

Workup

  1. temperatureat reflux for 73 hours
  2. temperaturereflux
  3. additionwas added
  4. temperatureAfter 16 hours reflux
  5. filtrationthe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe crude product was chromatographed on 200 g of silica gel
  8. washeluted with 15% ethyl acetate-toluene

Sources & evidence

ORD record
ord-7e7c95a3e8804ae593e4ee2ec361ea7f
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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