Yield:87188-50-9 96%

Reaction Conditions:

with dmap in acetonitrile at 20;

Steps:

Procedure A: Synthesis of O-tert-butyloxycarbonylated benzaldehydes

General procedure: To a solution of the hydroxybenzaldehyde (5.00 mmol) in dryacetonitrile (0.20 M), 0.10 equiv of dimethylaminopyridine was added.This was followed by addition under rapid stirring at room temperatureof 1.10 equiv of tert-butyldicarbonate for the monohydroxylated benzaldehydesand 2.20 equiv for the dihydroxylated benzaldehyde. Whenall the reactant had been fully tert-butyloxycarbonylated the solventwas evaporated at reduced pressure and the residue was dissolved inethyl acetate (100 mL) and washed with KHSO4 (1 M) and brine (3times 25 mL each). The organic layer was dried with MgSO4 and thesolvent evaporated at reduced pressure. The product obtained was thenrecrystallized or subject to column chromatography.

References:

Monteiro, Luís S.;Paiva-Martins, Fátima;Oliveira, Sandra;Machado, Inês;Costa, Marlene [Bioorganic Chemistry,2019,vol. 89,art. no. 102983]