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Synthesis of 2,5-dihydroxy[carboxy-14C]benzoic acid for electrochemical protein modification

✍ Scribed by Varghese John; Jonathan L. Vennerstrom; Thomas J. Holmes Jr.


Publisher
John Wiley and Sons
Year
1986
Tongue
French
Weight
165 KB
Volume
23
Category
Article
ISSN
0022-2135

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✦ Synopsis


The synthesis o f 2,5-dihydroxy[carboxy-14C]benzoic a c i d ( g e n t i s i c a c i d ) i s described. The procedure u t i l i z e d [carboxy-14C]salicylic a c i d as a s t a r t i n g m a t e r i a l . S a l i c y l i c a c i d was converted t o g e n t i s i c a c i d using potassium p e r s u l f a t e hydroxylation. The m i x t u r e o f h y d r o x y l a t i o n products i n t h i s r e a c t i o n was e a s i l y separated by UV-visual i z e d q u a r t z column chromatography t o o b t a i n t h e d e s i r e d isomer i n h i g h p u r i t y ( o v e r a l l y i e l d o f 38%).


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## Abstract In a first step, Δ1‐trans‐octenoic‐3‐^14^C acid was prepared by a Grignard reaction with BaCO~3~‐^14^C and 1‐bromo‐pentane, followed by reduction of the obtained hexanoic‐1‐^14^C acid to hexanal‐1‐^14^C via the n‐hexanol‐1‐^14^C. The produced hexanal‐1‐^14^C, by condensing with malonic