Potassium Carbonate → HCID 13753874, compound

HRID 1249009Notes

Reaction equation

HRID 1249009 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].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:26][O:25][C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][O:11][C:6]1[CH:5]=[CH:4][C:3]([C:12](=[O:14])[CH3:13])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 11107373Methyl 8-bromooctanoate

Product 1

HCID 13753874HCID 13753874, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.30 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone, 5.10 g of methyl 8-bromooctanoate and 4.55 g of anhydrous potassium carbonate in 100 ml of anhydrous acetone and 30 ml of anhydrous dimethyl formamide was stirred at reflux for 20 hours. The usual workup followed by purification by high pressure liquid chromatography using a solvent of 15% ethyl acetate-hexane gave 4.5 g (58% yield) of 8-(4-acetyl-3-hydroxy-2-propylphenoxy)octanoic acid methyl ester, the titled compound, mp 39°-41°, after crystallization from hexane.

Workup

  1. temperatureat reflux for 20 hours
  2. customThe usual workup followed by purification by high pressure liquid chromatography

Sources & evidence

ORD record
ord-f876f0bc756c493f94c21663cb861f05
Source dataset
uspto-grants-1986_12
Patent number
US04628115

Reaction notes

Loading…