Novel cinnamaldehyde compound having an azido group

#1. Field of the Invention

#The present invention relates to a novel cinnamaldehyde compound having an azido group. The compound is useful as an intermediate for providing a photosensitive moiety of a photoresist, and also as the photosensitive moiety.

#2. Description of the Related Art

#The present invention will next be described in detail by way of examples, which should not be construed as limiting the invention thereto.

#4-Azidobenzaldehyde (29.42 g, 0.2 mol) and propionaldehyde (12.22 g, 0.2 mol) were dissolved in a solvent mixture of isopropyl alcohol (100 g) and pure water (50 g). Under cooling in an ice bath, sodium hydroxide (2 g) dissolved in pure water (20 g) was added to the solution, and the mixture was stirred for two hours. Propionaldehyde (12.22 g, 0.2 mol) was added again to the mixture, and the resultant mixture was stirred for a further three hours. The formed precipitates were collected through filtration and dried, to thereby yield 23.14 g of p-azido-2-methylcinnamaldehyde as yellow crystals (yield: 62%). The compound thus obtained was identified on the basis of the 1H-NMR measurements shown in Table 1. 1 TABLE 1 ppm type H J value 9.57 s 1H 7.55 d 2H 8.6 7.22 s 1H 7.11 d 2H 8.5 2.08 s 3H

#The procedure of Example 1 was repeated, except that propionaldehyde (12.22 g) was replaced by butylaldehyde (14.42 g), to thereby yield 10.27 g of p-azido-2-ethylcinnamaldehyde (yield: 51 %). The compound thus obtained was identified on the basis of the 1H-NMR measurements shown in Table 2. 2 TABLE 2 ppm type H J value 9.53 s 1H 7.52 d 2H 8.4 7.15 s 1H 7.11 d 2H 8.4 2.56 q 2H 7.6 1.12 t 3H 7.6