Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
Acetyl ferulic acid chloride, (42)
To a solution of ferulic acid (5.000 g, 25.749 mmol) and DMAP (0.077 g, 0.643
mmol) in pyridine (10 ml) was acetic anhydride added (2.35 ml, 25 mmol) at 0 º C.
The reaction mixture was stirred for 4 hours and then poured onto crushed ice.
The aqueous phase was acidified with 2M HCl (50 ml) and extracted with
EtOAc/THF (3:1). The combined organic extracts were dried over MgSO 4 ,
filtered and the solvents were removed under reduced pressure. The residue was
washed with petroleum ether and evaporated under reduced pressure to give acetyl
ferulic acid (5.750 g, 94.54%) as a colourless powder. This product (5.550 g,
23.495 mmol) was suspended in toluene (100 ml) containing five drops of DMF.
Oxalyl chloride (4.36 ml, 50 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 42 as a pale
yellow powder (5.830 g, 95.8%). Rf 0.32 [chloroform: acetone (8:2)]; ν max
(KBr)/cm -1 : 1762 (C=O), 1639 (C Ar =C Ar ), 1218 (C-O); δ H (400 MHz, CDCl 3 ):
2.16 (3 H, s, 11-H), 3.71 (3 H, s, 12-H), 6.20 (1 H, d, J 16, 2-H), 6.95-6.97 (1 H,
m, Ph-H), 7.44 (1 H, d, J 16, 3-H); δ C (125 MHz, CDCl 3 ): 20.63 (C-11), 55.91 (C-
12), 111.19 (C-2), 119.21 (C-9), 121.12 (C-6), 123.16 (C-5), 133.56 (C-4), 141.25
(C-3), 143.73 (C-7), 151.35 (C-8), 168.48 (C-1), 168.70 (C-10).
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