6-Pentyl-2H-pyran-2-one

In 1940, Meijer (4) isolated Massoia lactone, 5.6-Dihydro-6-pentyl (2H)pyran-2-one (Dec-2-en-5-olide), C10HI6O2, from true massoia oil. In 1954, Abe and Sato (5) confirmed the structure. In 1968, Cavill al. (6) isolated a... 

Sn-beta, combined with hydrogen peroxide as oxidant, has the potential to substitute classical oxidants, for example peracids, in BV oxidations. As an example, the oxidation of delfone (2 pentylcyclopentanone) to d-decalactone (tetrahydro-6-pentyl-2H-pyran-2-one) is currently achieved using the corrosive peracetic acid. The resultant lactones have a creamy coconut-and peach-like aroma and are important flavor constituents of many types of fruit, and cheese and other dairy products. The lactones are also used in fragrances the two enantiomers have different aromas. Sn-beta was tested for this BV transformation in a stirred reactor. The desired lactone product was obtained in 86% yield in the presence of the Sn-beta catalyst. (302) This result demonstrated clearly that the combination of Sn-beta and hydrogen peroxide is an environmentally friendly alternative to the commonly used organic peracids, even in asymmetric synthesis. Instead of a stoichiometric amount of carboxyHc acid waste, water is produced as a side product from the oxidant. 

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