C-Alkylation and O-Alkylation in the Synthesis of Substituted Furoic Acids

Abstract

c The same compound was also obtained from methyl 4-arsonosophenoxyacetate and ethanolamine, yield 92%. methylol group was formed on the amide nitrogen and one on the arylamino nitrogen in the last two instances. The position of the methylol group on nitrogen rather than on the benzene ring was proved by hydrolysis to 4-arsonophenoxyacetic acid and N-4-arsonophenylglycine.4-Aminobenzenearsonous acid reacted with sodium formaldehyde bisulfite to yield a sulfomethyl derivative. 4-Cyano-and 4-hydrazinobenzenearsonous acid9•10 were obtained by reduction of the corresponding arsonic acids.

Catalytic Synthesis of Heterocycles. VI. Dehydrocyclization of o-Alkylbenzenes to Indoles

“…The ortho-para ratios for the nitration products of ethyl-and isopropylbenzene were determined and are compared below with that for toluene. 11 The value obtained for ethylbenzene agreed with that reported by Cline and Reid.12 These values fall in the expected order, with the isopropyl group causing much greater steric hindrance than the ethyl group.…”

Syntheses and Pyrolyses of Furan Analogues of α-Oxo-o-quinodimethanes. Formation of Methylenecyclobutenone and 1-Buten-3-yne via a Vinylcarbene–Cyclopropene Rearrangement

“…Acid 21 was prepared by condensation of ethyl 3-oxopentanonate ( 24 ) with 2-chloroacetaldehyde followed by hydrolysis of the resulting 2-ethyl-3-furoate ( 25 ) (Scheme ). Acid 22 was prepared by a method that has been previously reported . Acid 23 was prepared from refluxing 3-furoic acid ( 26 ) in basic D 2 O solution followed by methylation of the resulting 2,5-dideuterio-3-furoic acid ( 27 ) (Scheme ). …”

“…Anhydrides 12 and 13 were prepared from reactions of benzoyl chloride with the corresponding acids, 2-methyl-3-furoic acid ( 14) and 3-methyl-2-furoic acid (15), respectively (eqs 3 and 4). Acids 14 and 15 were prepared by using the methods that have been reported previously.…”

“…A procedure described for the preparation of 12 was followed for the reaction of 2,5-dimethyl-3-furoic acid with benzoyl chloride to give 91% yield of 19 : IR (CHCl 3 , cm –1 ) 1770 (CO), 1715 (C = O); 1 H NMR (CDCl 3 ) δ 8.18–8.14 (m, 2H), 7.67–7.62 (m, 1H), 7.55–7.48 (m, 2H), 6.28 (s, 1H), 2.60 (s, 3H), 2.27 (s, 3H); 13 C NMR (CDCl 3 ) δ 162.4 (C), 161.1 (C), 159.3 (C), 150.8 (C), 134.2 (CH), 130.3 (CH), 128.9 (C), 128.7 (CH), 113.2 (C), 105.9 (CH), 13.9 (CH 3 ), 13.1 (CH 3 ); HRMS Calcd for C 14 H 12 O 4 :244.0732. Found: 244.0738.…”

Probing Poly(n-butyl-methacrylate) Latex Film via Diffusion of Hydrophilic and Hydrophobic Dye Molecules

“…Probe Dyes. The hydrophobic dye, ACR-540 ( I ), was synthesized following the recipe given in refs and .

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