82027-27-8

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 201230-82-2 carbon monoxide 
• 594-19-4 tert.-butyl lithium 
• 100-52-7 benzaldehyde 
• 82027-26-7 {2,2-Dimethyl-1-[1-phenyl-meth-(Z)-ylidene]-propoxy}-trimethyl-silane 
• 6721-67-1 tert-butyl benzyl ketone 

Downstream Products

• 6050-53-9 1-hydroxy-3,3-dimethyl-1-phenyl-butan-2-one 
• 56346-02-2 α-hydroxy-1-neopentyl phenyl ketone 
• 82044-29-9 Methanesulfonic acid 3,3-dimethyl-2-oxo-1-phenyl-butyl ester 

Relevant academic research and scientific papers

Synthesis of α-Hydroxy Ketones by Direct, Low-Temperature, in Situ Nucleophilic Acylation of Aldehydes and Ketones by Acyllithium Reagents

The reaction of n-, sec-, and tert-butyllithium with CO at atmospheric pressure at -110 and -135 deg C in the appropriate solvent system in the presence of ketones and aldehydes generates the acyllithium, RC(O)Li, which reacts with the carbonyl compound to give the α-hydroxy ketone, generally in good yield.Reactions with aldehydes are limited in scope, working well with the t-BuLi-derived acyllithium reagents, but not with n-BuC(O)Li.

HIGH YIELD ACYL ANION TRANSFER REACTIONS: NUCLEOPHILIC ACYLATION OF ALDEHYDES

Aldehydes be may acylated to give R'CH(OH)C(O)R in good yield by the RLi/CO in situ procedure at very low temperatures.Examples are given of ketone acylations which demonstrate the advantages of 1:1 RLi/substrate stoichiometry and the use of lower (-135 deg C) temperature.