Potassium Carbonate → HCID 14329994, compound

HRID 2231465Notes

Reaction equation

HRID 2231465 reaction equation
[Cl:1][C:2]1[C:3]([OH:15])=[C:4]([CH2:12][CH2:13][CH3:14])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:16][O:17][C:18](=[O:38])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([O:30][CH2:31][CH2:32][CH2:33]Br)[C:22]=1[CH2:35][CH2:36][CH3:37].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:16][O:17][C:18](=[O:38])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([O:30][CH2:31][CH2:32][CH2:33][O:15][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8](=[O:10])[CH3:9])=[C:5]([OH:11])[C:4]=2[CH2:12][CH2:13][CH3:14])[C:22]=1[CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 133891721-(5-Chloro-2,4-dihydroxy-3-propylphenyl)ethan-1-oneHCID 53783998HCID 53783998, compound

Product 1

HCID 14329994HCID 14329994, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2 g (0.0088 mol) of 1-(5-chloro-2,4-dihydroxy-3-propylphenyl)ethanone, 3.39 g (0.0088 mol) of [4-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]acetic acid methyl ester and 1.8 g (0.013 mol) of anhydrous potassium carbonate in 150 ml of anhydrous acetone was stirred at reflux for 20 hours. An additional 1.0 g of potassium carbonate was added and reflux was continued for a total of 35 hours. The hot reaction mixture was filtered and filtrate was concentrated in vacuo to an oil which was dissolved in ethyl acetate and washed with 1N sodium hydroxide and sodium chloride solution. The crude oil obtained on concentration of the ethyl acetate solution was purified by HPLC, eluting with 30% ethyl acetate in hexane to yield 2.7 g (58% yield) of [4-acetyl-3-[3-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid methyl ester as a pale yellow oil.

Workup

  1. temperatureat reflux for 20 hours
  2. temperaturereflux
  3. customwas continued for a total of 35 hours
  4. filtrationThe hot reaction mixture was filtered
  5. concentrationfiltrate was concentrated in vacuo to an oil which
  6. dissolutionwas dissolved in ethyl acetate
  7. washwashed with 1N sodium hydroxide and sodium chloride solution
  8. customThe crude oil obtained on concentration of the ethyl acetate solution
  9. customwas purified by HPLC
  10. washeluting with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-10924feeb46a42c9b46351bc97d94ba4
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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