Sulfamic Acid → 4-Hydroxy-3-(methoxycarbonyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Sulfamic acid (1.83 g, 18.87 mmol) and 2-methyl-1-butene (1.20 ml, 11.10 mmol) were added to a solution of methyl 5-formyl-2-hydroxybenzoate (may be prepared as described in Description 106; 1 g, 5.55 mmol) in tetrahydrofuran (20 ml), water (20 ml) and dimethyl sulfoxide (20 ml). The solution was cooled to 0° C. and sodium chlorite (1.51 g, 16.65 mmol) in water (5 ml) was added. After 45 minutes at 0° C. the reaction the mixture was quenched with saturated Na2S2O3 solution (20 ml) and extracted with ethyl acetate (3×30 ml). The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a solid. 1.09 g (damp with DMSO/H2O).

Provenance & Evidence