m-Chloroperbenzoic acid → HCID 13375397, compound

Participants

Reaction Steps

A 1 L round bottom flask fitted with addition funnel and stirring bar was charged with 10-methylthio-9-anthracenecarbaldehyde (example 6A, 12.0 g, 48 mmol) and 450 mL of CH2Cl2. The resulting solution was cooled to 5° with an ice bath. A solution of MCPBA (Aldrich (85%), 9.64 g, 48 mmol) in 350 mL of CH2Cl2 was then added dropwise to the flask over 1 h. The reaction mixture was allowed to warm to RT over 1 h and then was washed with 5% NaHCO3 solution (2×500 mL), dried (Na2SO4), filtered, concentrated to 500 mL, and passed through SiO2 (250 g) using PhCH3 (5 L) eluting solvent. The desired material was then eluted from the SiO2 using EtOAc (2 L) as the eluting solvent. The solvent volume was reduced to 100 mL and then diluted to 700 mL with hexane. The resulting yellow solid was filtered and dried at 50° to give 11.98 g (94%) of 10-methylsulfinyl-9-anthracenecarbaldehyde mp 182°-184°, (C,H,S).

Provenance & Evidence