4,5-Dichlorophthalic anhydride → 2-Carbomethoxy 4,5-dichlorobenzoic acid

HRID 1681943Notes

Reaction equation

HRID 1681943 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][C:12]=1[Cl:13].[CH3:14][O-:15].[Na+]>CO>[C:6]([C:5]1[CH:11]=[C:12]([Cl:13])[C:2]([Cl:1])=[CH:3][C:4]=1[C:9]([OH:8])=[O:10])([O:15][CH3:14])=[O:7]

Participants

4

Reactant 2

HCID 703344,5-Dichlorophthalic anhydrideHCID 10942334Sodium Methoxide

Product 1

HCID 198042632-Carbomethoxy 4,5-dichlorobenzoic acidYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4,5-dichlorophthalic anhydride (1.0 g, 4.61 mmol) in 15 mL of methanol was added 0.25 g (9.22 mmol, 2.0 eq) of sodium methoxide. The suspension was stirred for 3 days and the methanol was removed in vacuo. The resultant white solid was suspended in 500 mL of CH2Cl2 and washed with 1N HCl. The organic phase was dried over anhydrous Na2SO4, filtered and the volatiles removed in vacuo to yield 1.06 g (92.5%) of the titled compound as a white powder.

Workup

  1. customthe methanol was removed in vacuo
  2. washwashed with 1N HCl
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-f6fa263ca617444e8bd8f293493ce640
Source dataset
uspto-grants-1992_12
Patent number
US05175164

Reaction notes

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