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Synthesis of [uniformly ring-14C]-labelled 4-hydroxybenzaldehyde, vanillin, and protocatechualdehyde

✍ Scribed by Rong Ji; Andreas Schäffer

Publisher
John Wiley and Sons
Year
2004
Tongue
French
Weight
105 KB
Volume
47
Category
Article
ISSN
0022-2135

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✦ Synopsis

Uniformly ring-14 C]-labelled 4-hydroxybenzaldehyde, vanillin, and protocatechualdehyde were synthesized from [ 14 C]-labelled phenol, guaiacol, and catechol with methyl dichloromethyl sulfide (CH 3 SCHCl 2 ) under Friedel-Crafts alkylation conditions in dichloromethane at À788C for 5 min (in the case of phenol and guaiacol) or at À208C for 1 min (in the case of catechol), by rapid addition of SnCl 4 to mixtures of the phenolic compound and CH 3 SCHCl 2 , followed by hydrolysis with HCl. Regioselective formylation (para to the -OH group) was achieved. The conversion rates were 96, 81, and 88% for 4-hydroxybenzaldehyde, vanillin, and protocatechualdehyde, respectively, and the yields of the recovered products after work-up amounted to 88, 75, and 83%, respectively. In the case of guaiacol, 17% of isovanillin was obtained as by-product. It was found that the presence of water or ethyl acetate in the reaction mixture, at a molar ratio of 60:1 (water:guaiacol) or 120:1 (ethyl acetate:guaiacol), had little influence on the yields under the reaction conditions. Factors influencing the yields are discussed in the study.

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