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

HRID 2231451Notes

Reaction equation

HRID 2231451 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=1[CH2:19][CH2:20][CH3:21])[CH3:2].[Br:23][CH2:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:26][CH2:25][CH2:24][Br:23])[C:10]=1[CH2:19][CH2:20][CH3:21])[CH3:2]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium Carbonate2×HCID 14330004Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoate

Product 1

HCID 143300054-[4-Acetyl-3-(3-bromopropoxy)-2-propylphenoxy]butanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 7.6 g of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoic acid ethyl ester, 25 ml 1,3-dibromopropane and 2.0 g of anhydrous potassium carbonate in 200 ml of anhydrous acetone was stirred at reflux. Additional 2.0 g portions of potassium carbonate were added at 3, 7, 21, 47 and 55 hours. After a total reflux time of 78 hours, the reaction mixture was filtered and the filtrate was concentrated in vacuo to yield 4-[4-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]butanoic acid ethyl ester as a slightly impure oil.

Workup

  1. temperatureat reflux
  2. filtrationAfter a total reflux time of 78 hours, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-121d57dee91e49c1889edd8f8a32df7c
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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