60696-49-3

Upstream product

• 84403-54-3 4-benzyloxy-N-butyl-benzamide 
• 109-73-9 N-butylamine 
• 99-96-7 4-hydroxy-benzoic acid 
• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 99-76-3 methyl 4-hydroxylbenzoate 

Downstream Products

• 847197-22-2 4-benzyloxy-benzoic acid 4-butylcarbamoyl-phenyl ester 

Relevant academic research and scientific papers

Access to Diarylmethanols by Wittig Rearrangement of ortho-, meta-, and para-Benzyloxy- N-Butylbenzamides

The N-butyl amide group, CONHBu, has been found to be an effective promoter of the [1,2]-Wittig rearrangement of aryl benzyl ethers and thus allow the two-step synthesis of isomerically pure substituted diarylmethanols starting from simple hydroxybenzoic acid derivatives. The method is compatible with a wide range of functional groups including methyl, methoxy, and fluoro, although not with nitro and, unexpectedly, is applicable to meta as well as ortho and para isomeric series.

Zn(OTf)2-promoted chemoselective esterification of hydroxyl group bearing carboxylic acids

Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I2, and a catalytic amount of Zn(OTf)2. Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from transesterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.

Liquid crystalline amides: Linear arrangement of rod-like molecules by lateral intermolecular hydrogen bonding and molecular shape effect

Bent- and straight-rod shaped liquid crystalline amides 1-3 were designed and synthesized, and their thermodynamic behaviors were investigated by polarized optical microscopy and differential scanning calorimetry, and their layer distances were measured by X-ray diffraction. Weak or strong hydrogen bonds were observed in variable-temperature FT-IR spectra for bent-rod shaped compounds 1 possessing a long alkoxy chain (OR2), straight-rod shaped compounds 2, and straight-rod shaped 3 in their smectic C, smectic C x, and smectic A phases, respectively. Thus, these liquid crystalline amides could generate linear molecular aggregates in their smectic layers by the lateral intermolecular hydrogen bonds.

Niobium pentachloride promoted conversion of carboxylic acids to carboxamides: Synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures

A practical method for the conversion of carboxylic acids to the corresponding carboxamides mediated by niobium pentachloride under mild conditions is described. The synthesis of the 4-aryl-1,2,3,4-tetrahydroisoquinoline alkaloid structures was accomplished via benzylic lithiation of N-methyl-3,4-dimethoxy-2-(4′-methoxybenzyl)benzamide.