Английская Википедия:2-Methylbut-3-yn-2-ol

Материал из Онлайн справочника
Перейти к навигацииПерейти к поиску

Шаблон:Chembox 2-Methylbut-3-yn-2-ol is the organic compound with the formula HC2C(OH)Me2 (Me = CH3). A colorless liquid, it is classified as an alkynyl alcohol.

Preparation and use

It arises from the condensation of acetylene and acetone. The addition can be promoted with base[1] (Favorskii reaction) or with Lewis acid catalysts.[2] 2-Methylbut-3-yn-2-ol is produced on an industrial scale as a precursor to terpenes and terpenoids.

Файл:IndustrialRouteGeranylAlc.png
2-Methylbut-3-yn-2-ol is an intermediate in this industrial route to geraniol.[3]

2-Methylbut-3-yn-2-ol also is used as a monoprotected version of acetylene. For example, after arylation at carbon, the acetone can be removed with base:[4]

HC2C(OH)Me2 + ArX + base → ArC2C(OH)Me2 + [Hbase]X
ArC2C(OH)Me2 → ArC2H + OCMe2

In this regard, 2-methylbut-3-yn-2-ol is used similarly to trimethylsilylacetylene.

References