Dicamba → Methyl (4-chlorobenzoyl)acetate

HRID 1607212Notes

Reaction equation

HRID 1607212 reaction equation
COC1C(C(O)=O)=C(Cl)C=CC=1Cl.[CH3:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:16].[CH3:24][O:25][C:26](=O)[O:27]C>C[O-].[Na+]>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([CH2:14][C:26]([O:25][CH3:24])=[O:27])=[O:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 3030DicambaHCID 7467P-ChloroacetophenoneHCID 12021Dimethyl Carbonate

Product 1

HCID 735885Methyl (4-chlorobenzoyl)acetate

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideCatalyst

Procedure

Alternatively, MDBA may be prepared by the carbomethoxylation of a ketone. For example, 4-chloracetophenone reacts with excess dimethylcarbonate using sodium methoxide as a catalyst to produce methyl 4-chlorobenzoylacetate as described in U.S. Pat. No. 3,950,381. NMR data was consistent with the structure.

Sources & evidence

ORD record
ord-e0b77945035e41e3af77b259cf77d116
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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