Potassium Carbonate → HCID 14330010, compound

HRID 2164947Notes

Reaction equation

HRID 2164947 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([OH:16])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2].[S:21]([O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33]OS(=O)(=O)C)(=[O:24])(=[O:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([O:16][CH2:33][CH2:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][S:21]([CH3:22])(=[O:23])=[O:24])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1107763580322-82-3HCID 13389144Ethyl (4-acetyl-3-hydroxy-2-propylphenoxy)acetate

Product 1

HCID 14330010HCID 14330010, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6228DimethylformamideSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

A mixture of 3.3 g (0.012 mole) of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid ethyl ester, 18.0 g (0.059) of triethyleneglycol dimesylate and 3.3 g (0.024 mole) of anhydrous potassium carbonate in 100 ml of anhydrous acetone and 45 ml of anhydrous dimethylformamide was stirred at reflux for 26 hours. The reaction mixture was concentrated in vacuo to yield an oil which was dissolved in 60% ethyl acetate-toluene and passed through a column of 60 g of silica gel. The eluent was concentrated in vacuo and purified by HPLC using 35% ethyl acetate-toluene to give 3.06 g (53% yield) of [4-acetyl-3-[2-[2-[2-[(methylsulfonyl)oxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 26 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto yield an oil which
  4. concentrationThe eluent was concentrated in vacuo
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-fdff84ae38dd499f8e54f45cad9106fc
Source dataset
uspto-grants-1985_03
Patent number
US04507498

Reaction notes

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