162147-97-9

Upstream product

• 7205-94-9 chloromethyl phenyl sulfoxide 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 51620-80-5 4-phenyl-1-(phenylsulfinyl)-2-butanone 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 33840-74-3 1-(phenylsulfinyl)propan-2-one 
• 930-69-8 sodium thiophenolate 

Downstream Products

• 41208-51-9 4-phenyl-1-(piperidin-1-yl)butan-1-one 
• 16537-11-4 tert-butyl 4-phenylbutanoate 
• 56379-64-7 phenyl 4-phenylbutanoate 
• 358349-85-6 isopropyl 4-phenylbutanoate 
• 20845-80-1 1-chloro-4-phenylbutan-2-one 
• 1821-12-1 4-Phenylbutyric acid 
• 2046-17-5 methyl 3-(benzyl)propanoate 

Relevant academic research and scientific papers

Dianion of sulfinylacetone as a synthetic equivalent of β-enolate of propionic acid: A novel synthesis of carboxylic acids from alkyl halides with three-carbon elongation

The reaction of the dianion of phenylsulfinylacetone with alkyl halides afforded β-keto sulfoxides, which were first chlorinated with hexachloroethane and then treated successively with KH and t-BuLi to give carboxylic acids in three-steps in moderate overall yields from the alkyl halides. This procedure affords a good method for a synthesis of carboxylic acids from alkyl halides with three-carbon elongation.

Ligand Exchange Reaction of Sulfoxides in Organic Synthesis: A New Synthesis of α-Chloroketones from Carbonyl Compounds with One-Carbon Homologation

A new procedure for one-carbon homologation of carbonyl compounds to α-chloroketones is described.Addition of the carbanion of dichloromethyl phenyl sulfoxide with ketones and aldehydes gave the adducts, chloro alcohols, in good yields.Treatment of the chloro alcohols with EtMgBr or lithium diisopropylamide gave one-carbon homologated α-chloroketones via β-oxido carbenoid rearrangement in moderate to good yields.One-carbon homologation of esters to α-chloroketones was realized via the ligand exchange reaction of the sulfinyl group of α-chloro α-sulfinyl ketones, which were synthesized from methyl esters and chloromethyl phenyl sulfoxide, with EtMgBr.

Ligand exchange reaction of sulfoxides in organic synthesis: A new method for one-carbon homologation of esters to carboxylic acids and esters via α- chloro α-sulfinyl ketones

Reaction of the Carbanion of chloromethyl phenyl sulfoxide with esters gave α-chloro α-sulfinyl ketones, which were treated with KH followed by t- BuLi to afford one-carbon homologated acids and esters in good to excellent yields.