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A convenient one step synthesis of 2,4‐dialkyl‐2‐hydroxy‐alkyl‐γ‐butyrolactone using lithium naphthalenide

1977; Wiley; Volume: 27; Issue: 4 Linguagem: Inglês

10.1002/jctb.5020270407

0375-9210

Tsutomu Fujita, Shôji Watanabe, Kyoichi SUGA, Masamoto Hokyo,

Inorganic and Organometallic Chemistry

Abstract One mole of propionic acid ( I ) reacts with 2 mol of 1,2‐butylene oxide ( II ) in the presence of lithium naphthalenide to give 4‐hydroxy‐2‐(2′‐hydroxybutyl)‐2‐methylhexanoic acid ( V ), which can be easily converted into 2‐(2′‐hydroxybutyl)‐2‐methyl‐4‐ethyl‐γ‐butyrolactone ( VII ). Similarly, 2,4‐dialkyl‐ and 2,4,4‐trialkyl‐2‐hydroxyalkyl‐γ‐butyrolactones were prepared from other carboxylic acids having two hydrogens at 2‐position and various epoxides.