The aldehyde jasmorange (1) was converted to the oxime (2), acylation of which by alkylcarboxylic acid anhydrides in the presence of HClO 4 or by acid chlorides in the presence of pyridine synthesized esters of jasmorange oxime 3-24 in 82-91% yields. Refluxing 3-24 in hexane converted them quantitatively into nitrile 25.The aldehyde jasmorange [2-methyl-3-(4-tolyl)propanal, 1] has a sharp fruity-balsamic fragrance with hints of watermelon and greens and is used in perfumes and fragrances [1]. Oximes of several natural compounds act as convenient synthons for preparing fragrances and biologically active compounds based on them [2,3].The goal of our work was to prepare a series of new esters from jasmorange oxime (2). Esters of jasmorange oxime 3-24 were synthesized by reacting 2 with anhydrides of alkylcarboxylic acids in the presence of catalytic amounts of HClO 4 (3-6) or with aklyl-and arylcarboxylic acid chlorides in the presence of pyridine (7-25). The yields of 3-24 were 82-91%. R = Me (3); Et (4); Pr (5); Me 2 CH (6); Me(CH 2 ) 3 (7); Me 2 CHCH 2 (8); Me 3 C (9); Me(CH 2 ) 4 (10); Me(CH 2 ) 5 (11); Me(CH 2 ) 6 (12); Me(CH 2 ) 7 (13); Me(CH 2 ) 8 (14); Me(CH 2 ) 11 (15); Me(CH 2 ) 16 (16); cycle-C 6 H 11 (17); C 6 H 5 (18); C 6 H 5 CH 2 (19); C 6 H 5 (CH 2 ) 2 (20); C 6 H 5 CHMeCH 2 (21); trans-C 6 H 5 CH=CH (22); MeO (23); EtO (24) The prepared esters 3-24 are derivatives of an aldehyde and are sensitive to heating, in contrast with esters based on ketone oximes [3]. Refluxing solutions of 3-24 in hexane converted them quantitatively into 1-(4-tolyl)-2-cyanopropane (25) in 98-100% yield via loss of the corresponding carboxylic acids.The structures of 2-25 were confirmed by elemental analysis; PMR, IR, and UV spectra; and cryoscopic molecularweight determination. According to PMR spectra, the products were 98 ± 1% pure. Elemental analyses and molecular-weight determinations of all synthesized compounds agreed with those calculated.The aromas of 2, esters 3-24, and nitrile 25 were assessed for organoleptic value by the Taste Council of the Accredited Monitoring Analytical Laboratory of OOO Tereza-Inter (Moscow). Table 1 lists the mean statistical taste data for the aromas of the products. Table 1 shows that all prepared compounds are highly interesting for potential use in perfumes and food production. The hint of fresh watermelon and fruit found in most of the synthesized compounds was important and promising for modern trends in perfume development.
