HCID 11097812, compound → HCID 10923769, compound

Participants

Reaction Steps

Into a slurry of 61.4 g (0.222 mol) of 1-(4-fluoro-3-methylphenyl)-6-hydroxymethyl-3,3,5,5-tetramethylcyclohexene in 330 ml of DMSO and 194 ml of triethylamine is poured a solution of 106.0 g (0.666 mol) of sulfur trioxide pyridine complex in 330 ml of DMSO. The reaction mixture is then stirred for 30 min. Ice (660 g) is added and the reaction mixture is extracted twice with 300 ml of hexanes. The extracts are then backwashed thrice with 280 ml of 10% HCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo at 40° C. to yield 57.1 g (94%) of 2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohex-2-enecarboxaldehyde suitable for use in the next step. A pure sample of 2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohex-2-enecarboxaldehyde can be obtained via column chromatography on silica gel.

Provenance & Evidence