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

HRID 1886466

Reaction equation

HRID 1886466 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-852047df22c64977a21f70ec46b553e2
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Linked notes

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