149764-54-5

Basic information

• Product Name: 4-chloro-3-hydroxy-1,3-diphenylbutan-1-one
• Synonyms: 4-chloro-3-hydroxy-1,3-diphenylbutan-1-one
• CAS NO: 149764-54-5
• Molecular Weight: 274.747
• Mol File: 149764-54-5.mol

Chemical Properties

• CAS DataBase Reference: 4-chloro-3-hydroxy-1,3-diphenylbutan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-3-hydroxy-1,3-diphenylbutan-1-one(149764-54-5)
• EPA Substance Registry System: 4-chloro-3-hydroxy-1,3-diphenylbutan-1-one(149764-54-5)

Safety Data

• Hazardous Substances Data: 149764-54-5(Hazardous Substances Data)

Upstream product

• 17851-99-9 1-phenyl-2-tributylstannyl-1-ethanone 
• 532-27-4 1-chloroacetophenone 
• 17851-98-8 1-phenyl-1-(tributylstannyloxy)ethene 
• 1052762-47-6 lithium 1-phenylethenolate 
• 98-86-2 acetophenone 

Downstream Products

• 495-71-6 phenacylacetophenone 

Relevant articles and documents

Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate

An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported.

Cross-coupling reaction of α-chloroketones and organotin enolates catalyzed by zinc halides for synthesis of γ-diketones

The reaction of tin enolates 1 with α-chloro- or bromoketones 2 gave γ-diketones (1,4-diketones) 3 catalyzed by zinc halides. In contrast to the exclusive formation of 1,4-diketones 3 under catalytic conditions, uncatalyzed reaction of 1 with 2 gave aldol-type products 4 through carbonyl attack. NMR study indicates that the catalyzed reaction includes precondensation between tin enolates and α-haloketones providing an aldol-type species and their rearrangement of the oxoalkyl group with leaving halogen to produce 1,4-diketones. The catalyst, zinc halides, plays an important role in each step. The carbonyl attack for precondensation is accelerated by the catalyst as Lewis acid and the intermediate zincate promotes the rearrangement by releasing oxygen and bonding with halogen. Various types of tin enolates and α-chloro and bromoketones were applied to the zinc-catalyzed cross-coupling. On the other hand, the allylic halides, which have no carbonyl moiety, were inert to the zinc-catalyzed coupling with tin enolates. The copper halides showed high catalytic activity for the coupling between tin enolates 1 and organic halides 7 to give γ,δ-unsaturated ketones 8 and/or 9. The reaction with even chlorides proceeded effectively by the catalytic system.

Facile Control of Regioselectivity in the Reaction of Tin Enolates with α-Halogeno Carbonyls by Additives

Tin enolates 1 reacted with α-halogeno ketones 2 and esters 10 to give a variety of 1,4-diketones 3 and γ-keto esters 11, respectively, in the presence of appropriate additives such as hexamethylphosphoric triamide (HMPT), tributylphosphine oxide and tetrabutylammonium bromide, while complexation of these additives with tributyltin bromide allowed catalytic production of β-keto oxiranes 4 instead of 3.The reaction mechanism for the preparation of 1,4-diketone 3 is discussed.