Potassium Carbonate → HCID 21649025, compound

HRID 1885263Notes

Reaction equation

HRID 1885263 reaction equation
[Cl:1][C:2]1[C:10]([OH:11])=[C:9]([OH:12])[C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>CN(C)C=O>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:5][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([Cl:13])[C:9]([O:12][CH2:26][C:25]3[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)=[C:10]([O:11][CH2:4][C:3]3[CH:7]=[CH:8][C:9]([O:17][CH3:14])=[CH:10][CH:2]=3)[C:2]=2[Cl:1])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 50914Benzoic acid, dichloro-3,4-dihydroxy-HCID 1650214-Methoxybenzyl bromide2×

Product 1

HCID 21649025HCID 21649025, compoundYield 156.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-dichloro-3,4-dihydroxybenzoic acid (2.4 g) in dimethylformamide (20 ml) are added potassium carbonate (4.90 g: 3.6 Eq.) and p-methoxybenzyl bromide (7.14 g: 3.6 Eq.). To the stirring mixture are added at room temperature every 2 hours potassium carbonate (1.6 g: 1.2 Eq.) and p-methoxybenzyl bromide (2.3 g: 1.2 Eq.). The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel chromatography giving 2.5-dichloro-3,4-bis(p-methoxybenzyloxy)benzoic acid p-methoxybenzyl ester (4.9 g) from the fraction eluting with toluene: ethyl acetate (40:1). Yield: 78%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-fe0f48b587b747739ff3ca8013dd6f14
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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