Trichloroisocyanuric Acid → 4-Methylcatechol

Participants

Reaction Conditions

Reaction Steps

TCCA (16.7 g, 72 mmol) was added to a solution of 4-fluoro-1-methyl-2-nitrobenzene (12.4 g, 80 mmol) in CH3CO2H/H2SO4 (80 mL/80 mL). The mixture was heated to 70° C. and stirred overnight. After cooling to room temperature, the reaction mixture was poured into ice water (1000 mL) and extracted with DCM (2×200 mL). The combined organic phase was washed with brine and concentrated in vacuo. The residue was purified by column chromatography (PE: EA=50:1) to give compound 1 (5.0 g, 33.1%) as a yellow oil.

Provenance & Evidence