Potassium Carbonate → HCID 54210320, compound

HRID 1885260Notes

Reaction equation

HRID 1885260 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([Cl:11])=[CH:9][C:8]([OH:12])=[C:7]([OH:13])[CH:6]=1)[CH3:2].[C:15](=[O:18])([O-])[O-].[K+].[K+].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[C:10]([Cl:11])=[CH:9][C:8]([O:12][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)=[C:7]([O:13][CH2:4][C:5]2[CH:10]=[CH:9][C:8]([O:18][CH3:15])=[CH:7][CH:6]=2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 54196354HCID 54196354, compound

Product 1

HCID 54210320HCID 54210320, compoundYield 198.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dihydroxy-6-chlorobenzoic acid ethyl ester (52.7 g: 243 mMol.) in dimethylformamide (170 ml) are added potassium carbonate (105 g; 3.1 Eq.) and p-methoxybenzyl bromide (151 g: 3.1 Eq.), and the mixture is stirred at room temperature for 4 hours. The reaction mixture is diluted with ice water and filtered to collect the resulting precipitate, which is washed with methanol and water to give 6-chloro-3,4-bis(p-methoxybenzyloxy)benzoic acid ethyl ester (110 g). Yield: 99%.

Workup

  1. filtrationfiltered
  2. customto collect the resulting precipitate, which
  3. washis washed with methanol and water

Sources & evidence

ORD record
ord-a04188c3727544e48cfc80ef8f770e06
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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