m-Chloroperbenzoic acid → HCID 13375397, compound

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Reaction Steps

A 1 L RB flask fitted with addition funnel and stirring bar was charged with 10-methylthio-9-anthracenecarbaldehyde (example 3A, 12.0 g, 48 mmol) and 450 mL of CH2Cl2. The resulting solution was cooled to 5° with an ice bath. A solution of m-chloroperbenzoic acid (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 a plug of SiO2 (250 g) using PhCH3 (5 L) as the eluting solvent. The desired material was then eluted from the SiO2 using EtOAc (2 L) as 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