Potassium Carbonate → HCID 14329993, compound

HRID 2164937Notes

Reaction equation

HRID 2164937 reaction equation
[Br: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]([Br: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 133891711-(5-Bromo-2,4-dihydroxy-3-propylphenyl)ethan-1-oneHCID 53783998HCID 53783998, compound

Product 1

HCID 14329993HCID 14329993, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2 g (0.0073 mol) of 1-(5-bromo-2,4-dihydroxy-3-propylphenyl)-ethanone, 2.84 g (0.0073 mol) of [4-acetyl-3-(3-bromopropoxy)-2-propylphenoxy]acetic acid methyl ester and 1.52 g (0.011 mol) of anhydrous potassium carbonate in 150 ml of anhydrous acetone was stirred at reflux for 20 hours. An additional 1 g of potassium carbonate was added and reflux was continued for a total of 35 hours. The hot reaction mixture was filtered and the filtrate was concentrated in vacuo to a oil which was dissolved in ethyl acetate and washed with 1N sodium hydroxide and sodium chloride solution. The crude product was purified by HPLC, eluting with 25% ethyl acetate in hexane to yield 2.33 g (55% yield) of [4-acetyl-3-[3-(4-acetyl-6-bromo-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. concentrationthe filtrate was concentrated in vacuo to a oil which
  6. dissolutionwas dissolved in ethyl acetate
  7. washwashed with 1N sodium hydroxide and sodium chloride solution
  8. customThe crude product was purified by HPLC
  9. washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-40f07b24aa9d4faaaee0ae0d2ccbbd78
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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