Potassium Carbonate → HCID 14329986, compound

HRID 2231484Notes

Reaction equation

HRID 2231484 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([OH:11])[CH:5]=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].[CH2:15]([O:17][C:18](=[O:44])[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][CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39]I)[C:22]=1[CH2:41][CH2:42][CH3:43])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:15]([O:17][C:18](=[O:44])[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][CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][O:11][C:6]2[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=2[CH2:8][CH2:9][CH3:10])[C:22]=1[CH2:41][CH2:42][CH3:43])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 14330016HCID 14330016, compound

Product 1

HCID 14329986HCID 14329986, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.00 g (0.0052 mole) of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 2.78 g (0.0052 mole) of [4-acetyl-3-[4-(4-iodobutoxy)butoxy]-2-propylphenoxy]acetic acid ethyl ester and 1.44 g (0.010 mole) of anhydrous potassium carbonate in 75 ml of anhydrous acetone was stirred at reflux for 18 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by HPLC using 35% ethyl acetate-hexane to give 2.72 g (87% yield) of [4-acetyl-3-[4-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butoxy]butoxy]-2-propylphenoxy]acetic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-5d6046d31e394102a38c60a891101e02
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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