m-Chloroperbenzoic acid → HCID 58240633, compound

Participants

Reaction Steps

A solution of 2,2,7,7-tetramethyltricyclo[6.2.1.01.6]undecen-5-yl acetates described in Example 1a (2a+2b, 30.0 g, 95% pure, 0.11 mol) and MCPBA (36.5 g, 77% pure, 0.16 mol) in methylene chloride (300 ml) was stirred at room temperature (r. t.) for 24 h. An additional portion of MCPBA (10.0 g, 0.045 mol), added after 17 h, was necessary to complete the reaction. The reaction mixture was washed with aqueous sodium hydroxide solution and then water to pH 7 and negative peroxide test (KI paper), concentrated in vacuo and purified by flash chromatography (MTBE/hexane 1:9) to give a 61+37% mixture of 2,2,8,8-tetramethyl-5-oxatetracyclo[7.2.1.01.7.04.6]dodec-6-yl acetate (3) and the isomeric 2,2,8,8-tetramethyl-6-oxatetracyclo[7.2.1.01.7.05.7]dodec-5-yl acetate (14.8 g, 30+18% yield, pale yellow waxy solid). This mixture was used in the next steps without further purification.

Provenance & Evidence