Etherification Reactions of Furfuryl Alcohol in the Presence of Orthoesters and Ketals: Application to the Synthesis of Furfuryl Ether Biofuels

Abstract

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Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media

“…It must be mentioned that the low temperature applied improved selectivity by decreasing the production of hydrolysis products, and the competing polymerization reactions resulting in humin by-products. 158 In 2015, Zhang et al utilized ZrO 2 supported Pd(OH) 2 (Pd(OH) 2 /ZrO 2 ) as a new catalytic system for the synthesis of aryl ethers (137) via the reaction of substituted cyclohexanones (136) with orthoesters (4, 5, 127) as both dehydrating and nucleophilic reagents under an atmospheric pressure of oxygen (0.5 MPa) at 140 C for 6 h (Scheme 36). It was found that in the presence of TMOF (4) reagent, the corresponding aryl ethers were obtained in moderate to good yields.…”

“…166 The cross-coupling reaction of aryl iodides (155) with 3,3,3triethoxy-1-propyne (156) using dichlorobis(triphenylphosphine) palladium [(PPh 3 ) 2 PdCl 2 ] and cuprous iodide (CuI) in triethylamine (Et 3 N) at room temperature led to the production of 3,3,3-triethoxy-1-aryl-1-propyne within 1-4 h, which aer isolation was subsequently reacted with a catalytic amount of p-TSA in benzene at room temperature for 12 h to yield the ethyl arylpropiolates (157) (Scheme 42). 167 Padmapriya and co-workers reported the alkylation of sulfonic acids (158) (163,164) and triic acid (TfOH) at À20 to 40 C, yielding the corresponding alkyl 2-(naphthalen-1-yl)propanoate (165) (Scheme 45). In this reaction the effect of different parameters, such as the type of catalyst, catalytic amounts of Lewis acid, the nature of the orthoester, and temperature were investigated.…”

Orthoesters: Multiple Role Players in Organic Synthesis

“…Recently Chaffey et al . reacted furfuryl alcohols with TMOF and TEOF in the presence of catalytic amounts of zeolite secondary mobil–5 ZSM‐5 (Si/Al ratio=30 : 1, ZSM‐5‐(30)) in short alcohols or dimethyl carbonate DMC (as a substitute for traditional solvents).…”

Solid Acids for the Reaction of Bioderived Alcohols into Ethers for Fuel Applications

“…The unraveled potential of the interaction of orthoester with alcohols in the presence of various solid acids, has been very recently exploited for the preparation of furanic ethers [64].…”