31928-96-8

Upstream product

• 30182-67-3 1,3-Cyclohexanedione 
• 107-18-6 allyl alcohol 
• 504-02-9 1,3-cylohexanedione 
• 106-95-6 allyl bromide 
• 53293-00-8 hex-5-ynoic acid 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 877823-41-1 3-(hexyloxy)cyclohex-2-en-1-one 
• 16493-04-2 3-butanoxycyclohex-2-en-1-one 
• 16807-60-6 3-methoxycyclohex-2-en-1-one 

Downstream Products

• 504-02-9 1,3-cylohexanedione 
• 448956-67-0 3-(allyloxy)-4-bromophenol 
• 83613-31-4 3-(allyloxy)-4-chlorophenol 
• 31929-05-2 3-Acetoxy-2-allyl-2-cyclohexen-1-on 

Relevant academic research and scientific papers

Rapid and Multigram Synthesis of Vinylogous Esters under Continuous Flow: An Access to Transetherification and Reverse Reaction of Vinylogous Esters

An environmentally benign approach for the synthesis of vinylogous esters from 1,3-diketone and its reverse reaction under continuous-flow has been developed with alcohols in the presence of inexpensive Amberlyst-15 as a catalyst. This methodology is highly selective and general for a range of cyclic 1,3-dicarbonyl compounds which gives a library of linear alkylated and arylated vinylogous esters in good to excellent yield under solvent and metal free condition. Furthermore, the long-time experiment in a continuous-flow up to 40 h afforded 8.0 g of the vinylogous ester with turnover number (TON) = 28.6 and turnover frequency (TOF) = 0.715 h-1 using Amberlyst-15 as a catalyst. Furthermore, a continuous-flow sequential transetherification of vinylogous esters with various alcohols has been achieved in high yield. Reversibly, this vinylogous ester was deprotected or hydrolyzed into ketone using environmentally benign water as a solvent and Amberlyst-15 as a catalyst under continuous-flow process.

Reversible chemoselective transetherification of vinylogous esters using Fe-catalyst under additive free conditions

An additive/Br?nsted acid/base free, highly efficient and chemoselective transetherification of electron deficient vinylogous esters and water mediated de-alkylation using an earth-abundant Fe-catalyst under very mild reaction conditions is described. This reaction is highly selective to primary alcohols over secondary alcohols, has good functional group tolerance, is scalable to gram scale and a purification free sequential transetherification in a continuous flow mode is demonstrated.

Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2- cyclohexenones proceeds in good yields (58-90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.

Zinc-mediated alkylation and acylation of 1,3-dicarbonyl compounds

1,3-Dicarbonyl compounds undergo smooth allylation, benzylation, propargylation, and acylation with halides using metallic zinc in DMF at 60 °C to afford the corresponding allyl, benzyl, 2-propynyl, and acylated 1,3-diesters in good yields. In the case of cyclic 1,3-diketones, the corresponding enol ethers are obtained as sole products instead of C-alkylation.

Iron(III) tosylate in the preparation of dimethyl and diethyl acetals from ketones and β-keto enol ethers from cyclic β-diketones

An efficient method for conversion of ketones to their corresponding dimethyl and diethyl acetals and of cyclic β-diketones into β-keto enol ethers using Fe(OTs)3 as a catalyst is described. Copyright Taylor & Francis Group, LLC.

An efficient conversion of β-diketones into β-keto enol ethers with P2O5/SiO2 under solvent-free conditions

P2O5/SiO2 was found to be an efficient reagent for converting cyclic-β-diketones into their corresponding β-keto enol ethers at room temperature under solvent-free conditions.

B(C6F5)3-catalyzed synthesis of β-keto enol ethers from β-diketones

Efficient and practical synthesis of β-keto enol ethers from diketones catalyzed by B(C6F5)3 at room temperature has been described. Georg Thieme Verlag Stuttgart.

Microwave assisted rapid synthesis of 3-alkoxy-2-cyclohexen-1-ones from 1,3-cyclohexanedione

Synthesis of 3-alkoxy-2-cyclohexen-1-ones from 1,3-cyclohexanedione with various alcohols has been achieved under microwave irradiation conditions within 7 min.

Solvent free rapid synthesis of 3-alkoxycyclohex-2-en-1-one from 1,3-cyclohexanedione promoted by indium(in) chloride/silica gel

A convenient and environmentally friendly method for the synthesis of 3-alkoxycyclohex-2-en-1-one 1 from cyclohexane-1,3-dioneonthe surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent has been reported CSIRO 2005.

Tetraphenylstibonium Methoxide Promoting C-Alkylation of 2-Substituted Cyclic 1,3-Diketones

Selective C-alkylation of 2-methyl-1,3-cyclopentanedione and 2-methyl-1,3-cyclohexanedione was performed by using tetraphenylstibonium methoxide (Ph4SbOMe).The presence of a substituent at the 2-position was essential for C-alkylation.