References
- Kaye , P. T. and Whittal , R. D. 1991 . S. Afr. J. Chem. , 44 : 30
- Kaye , P. T. and Whittal , R. D. S. Afr. J. Chem. , in the press
- Litkei , G. and Patonay , T. 1983 . Acta Chimica Hungarica , 114 : 47
- Reddy , M. S. , Krupadanam , G. L. D. and Srimannarayana , G. 1989 . Org. Prep. Proced. Int. , 21 : 221
- Brown , D. W. , Floyd , A. J. and Sainsbury , M. 1988 . ‘Organic Spectroscopy’ , 97ff Chichester : Wiley . Using correlation tables by
- 13C Spectra were edited by APT (50 MHz) or ORD (125 MHz) techniques. In the case of the parent system 2a, signal assignments are supported by 2-dimensional (HETCOR and COSY) analyses
- Analytical data for these methyl esters are as follows:- Methyl 3- (5-bromo-2-hydroxyphenoxy)-3-phenylpropanoate 6g, m. p. 90–91°C (Found: m/z 350.015. C16H15O4 79Br Requires: M +, 350.015); δ H (200 MHz; CDCl3) 2.78 and 3.17 (2H, 2 × dd, 2-H), 3.77 (3H, s, Me), 5.27 (1H, dd, 3-H), and 6.59 and 6.81 (2H, 2xd, ArH), 6.91 (1H; dd, ArH) and 7.36 (5H, m, ArH); δ c (50 MHz; CDCl3) 42.09 (C-2), 52.66 (Me), 80.16 (C-3), 110.80, 112.64, 117.74, 123.17, 126.97, 127.47, 129.35, 139.12, 145.43 and 148.39 (ArC), and 173.11 (CO);v max (KBr disc) 3295 (OH) and 1715 cm−1 (CO). Methyl 3-(5-fluoro-2-hydroxyphenoxy)-3-phenylpropanoate 6h, m. p. 70–71°C (Found: m/z 290.095. C16H15O4F Requires: M +, 290.095); δ H (60 MHz; CDl3) 2.9 and 3.1 (2xH, 2xd, 2-H), 3.7 (3H, s, Me), 5.35 (1H, dd, 3-H), 6.2 − 7.0 (3H, m, ArH) and 7.45 (5H, s, ArH); v max (KBr disc) 3410 (OH) and 1710 cm−1 (CO)
- Whittal , R. D. 1990 . MSc thesis Rhodes
- March , J. 1985 . ‘Advanced Organic Chemistry: Reactions, Mechanisms, and Structure’, , 3rd Edn. , 986 New York : McGraw-Hill . and 990
- In other cases purification was typically effected by flash chromatography on silica (elution with ethyl acetate-hexane) and/or recrystallisation from MeOH. (The possibility of lactone methanolysis should, however, be noted)