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Two-three steps syntheses of [14C-ring]o-xylene, [14C-ring]o-toluic acid; [14C-ring]-phthalic acid from [14C] barium carbonate

✍ Scribed by S. De Suzzoni; J. P. Noel

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
293 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Cocyclotrimerisation of [^14^C~2~] acetylene with 2‐butyne gave [3,4,5,6‐^14^C~4~] ortho‐xylene (50% overall yield based on [^14^C] BaCO~3~). 93% Nitric acid oxidation at 145°C for 55 hours of the crude [3,4,5,6‐^14^C~4~] ortho‐xylene gave [3,4,5,6‐^14^C~4~] ortho‐toluic acid (25% overall yield based on [^14^C] BaCO~3~). Under the same set of reaction conditions but in a sealed tube the crude [3,4,5,6‐^14^C~4~] ortho‐xylene gave [3,4,5,6‐^14^C~4~] phthalic acid (50% overall yield based on [^14^C] BaCO^3^) (specific activity 1.6 GBq. mmol^−1^).

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## Abstract p‐Toluic acid‐ring‐^14^C was synthesized by the Friedel‐Crafts p‐carbamylation of toluene‐ring‐^14^C with N,N‐disubstituted carbamyl chloride and subsequent hydrolysis. The radiochemical yield was 61%. An attempt was made to apply this method for the synthesis of benzoic acid‐ring‐^14^C