Potassium Carbonate → HCID 13753874, compound

HRID 652508Notes

Reaction equation

HRID 652508 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-746631b6538c4f16b3b2462261a25bd2
Source dataset
uspto-grants-1987_06
Patent number
US04672066

Reaction notes

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