69217-50-1Relevant academic research and scientific papers
Solid sodium hydroxide - THF, convenient system for synthesis esters of glycidic acids by darzens condensation
Gadaj,Kowalkowska,Jonczyk
, p. 577 - 584 (2008/09/19)
Isopropyl- and tert-butylchloroacetate react with carbonyl compounds in the presence of powdered sodium hydroxide in THF, without a catalyst, giving substituted glycidates. The process is applied for preparation of glycidates from ketones, hitherto unavailable by phase-transfer catalyzed Darzens condensation.
Convenient synthesis of t-butyl Z-3-substituted glycidates under conditions of phase-transfer catalysis
Jonczyk, Andrzej,Zomerfeld, Tomasz
, p. 2359 - 2361 (2007/10/03)
Reactions of mixtures of t-butyl E- and Z-3-substituted glycidates 1a-h with 50% aq. sodium hydroxide and a catalyst, benzyltriethylammonium chloride, TEBAC in dichloromethane (phase-transfer catalysis, PTC) led to preferential hydrolysis of the E-isomers to afford pure (90-98%) t-butyl Z-3-substituted glycidates 1a-i in good yields; PTC cleavage of glycidates additionally substituted at C-2, 1g or C-3, 1h,i suggests that an aryl group in the Z isomers hampers attack of HO- on the carbonyl carbon atom. As described in the literature, the diastereoselective PTC synthesis of Z-3-substituted glycidates and glycidonitriles consists of fast hydrolysis of E isomers present in mixtures with Z ones.
