Acetone → HCID 131714176, compound

HRID 2231455Notes

Reaction equation

HRID 2231455 reaction equation
C(OC(=O)[CH:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[C:10]([OH:17])[C:9]=1[CH2:18][CH2:19][CH3:20])[CH3:6])C.[Br:22][CH2:23][CH2:24][CH2:25]Br.[C:27](=[O:30])([O-])[O-:28].[K+].[K+].[CH3:33][C:34](C)=O>>[CH2:33]([O:28][C:27](=[O:30])[CH2:6][CH2:5][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[C:10]([O:17][CH2:25][CH2:24][CH2:23][Br:22])[C:9]=1[CH2:18][CH2:19][CH3:20])[CH3:34]

Participants

5

Reactant 4

HCID 180AcetoneHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 14330021Ethyl 2-(4-acetyl-3-hydroxy-2-propylphenoxy)propanoate

Product 1

HCID 131714176HCID 131714176, compound

Procedure

A mixture of 6.4 g of racemic-(4-acetyl-3-hydroxy-2-propylphenoxy)-alpha-methylacetic acid ethyl ester, 22 ml of 1,3-dibromopropane and 4.5 g of anhydrous potassium carbonate in 175 ml of anhydrous acetone was stirred at reflux for 52 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to 9.0 g of racemic-[4-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]methylacetic acid as a yellow oil.

Workup

  1. temperatureat reflux for 52 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to 9.0 g of racemic-[4-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]methylacetic acid as a yellow oil

Sources & evidence

ORD record
ord-3ab0a2478ba34a67a1028c386eb097fd
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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