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Synthesis of 1,3,5-trimethoxy[1-14C]benzene

✍ Scribed by Helen T. Lee; Annette M. Travalent; Peter W. K. Woo

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
220 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Utilizing the facile acylative annulation of 2‐methoxypropene with [1‐^14^C]malonyl dichloride (5), the synthesis of 1,3,5‐trimethoxy[1‐^14^C]benzene (8) was accomplished through a seven‐step sequence starting from potassium [^14^C]cyanide with an overall yield of 60%.

Thus, reaction of bromoacetic acid with potassium [^14^C]cyanide gave sodium [^14^C]cyanoacetate (1). Hydrolysis of 1 with sodium hydroxide solution provided the sodium salt of [1‐^14^C]malonic acid (2). Treatment of 2 with calcium chloride gave the calcium salt 3, which was acidified with concentrated sulfuric acid in ether to give [1‐^14^C]malonic acid (4). Reaction of 4 with oxalyl chloride in refluxing ether gave [1‐^14^C]malonyl dichloride (5). Annulative acylations of 2‐methoxypropene with 5 gave the crucial intermediate 5‐methoxy[1‐^14^C]resorcinol (7), together with 4‐hydroxy‐6‐methyl‐[2 (or 4)‐^14^C]2H‐pyran‐2‐one (6), in a ratio of 3: 1. However, 6 could be advantageously converted to 7a by initial 0‐methylation with dimethyl sulfate, followed by rearrangement of the product, 4‐methoxy‐6‐methyl[2(or 4)‐^14^C]2H‐pyran‐2‐one (6a), upon treatment with sodium methoxide. Finally, bis‐0‐methylation of 7 and 7a with dimethyl sulfate in refluxing acetone gave the title compound 8.

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