Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
3, 4-dimethoxycinnamic acid chloride, (44)
3, 4-dimethoxycinnamic acid (5.000 g, 24.014 mmol) was suspended in toluene
(100 ml) containing five drops of DMF. Oxalyl chloride (4.31 ml, 49.26 mmol)
was added at -5 º C and stirred for 2 hours. The reaction mixture was stirred
additional 15 hours at room temperature, filtered and the solvent was removed
under vacuum to give the title compound 44 as a bright yellow powder (5.090 g,
93.56%). Rf 0.45 [chloroform: acetone (8:2)]; ν max (KBr)/cm -1 : 1682 (C=O), 1626
(C Ar =C Ar ), 1141 (C-O); δ H (400 MHz, CDCl 3 ): 3.93 (3 H, s, 10-H), 3.97 (3 H, s,
11-H), 6.48 (1 H, d, J 16, 2-H), 6.88 (1 H, d, J 8.4, 9-H), 7.05 (1 H, d, J 2, 6-H),
7.17 (1 H, dd, J 8.2 and 1.6, 5-H), 7.29 (1 H, d, J 16, 3-H); δ C (125 MHz,
CDCl 3 ):55.99 (C-10), 56.08 (C-11), 109.87 (C-9), 111.13 (C-6), 114.82 (C-2),
123.19 (C-5), 127.13 (C-4), 147.05 (C-3), 149.37 (C-8), 151.78 (C-7), 171.92 (C-
1).
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