A NOVEL METHOD OF SYNTHESIS OF ALKYL α-CYANOACRYLOYL GLYCOLATES

This article was downloaded by: [ ] On: 18 August 2011, At: 03:34 Publisher: Taylor & Francis Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK Organic Preparations and Procedures International Publication details, including instructions for authors and subscription information: http://www.tandfonline.com/loi/uopp20 A NOVEL METHOD OF SYNTHESIS OF ALKYL m-2) Weak acidic catalyst | 0.5-1 .0mmHg cozcnzcuzn 170.21 1° R = Me. El. i—Pr. 1'—EII. i~Am Because the monomer polymerize: readily at room temperature, the condensation of fomtaldehyde with alkyl a-cyanoacetyl glycolales is best canied out under weakly acidic conditions. The lower molecular weight of the polymers and the narrower molecular weight distribution, led to smooth depolymerizalion on distillation to give higher yields of monomers of excellent purity. TABLE 1. Yields. Physical Constants and ‘H NMR Data of Alkyl 11-Cyanoaoetyl Glycolates (1) R bp. (“C /rmnflg) Yie|d(%) ‘H NMR Data 5 (ppm) CH1 l06—l I0/1.0 81.5 3.75 (S, 3H,-CH1), 4. 64 (5, 2H, —CO0CH._,C0—), 3.90 (NCCH2C0-) C211, 108-1 12/1.0 113.2 1.25 (1. 3H. cH,§u,), 4.20 (m, 211, .g2c1-1,), 4. 62 (s. 2H, -C00CH2C0)y3,58 (5. 2H, NCCH1-] 1-0111, 109413/1.0 112.1 1.25 Id, s11,—c11 @921, 4.10 [m. 1H.—Q(CH_,)2], 4. 60 (S, 2H,-COOCHYCO-). 3.50 (S, 2H. NCCH.2