3,4-DIACETOXY-BENZOIC ACID synthesis
- Product Name:3,4-DIACETOXY-BENZOIC ACID
- CAS Number:58534-64-8
- Molecular formula:C11H10O6
- Molecular Weight:238.19
Yield:58534-64-8 95%
Reaction Conditions:
with pyridine at 0; for 2 h;Inert atmosphere;
Steps:
3.4.1.5. 3,4-Diacetoxybenzoic acid (12)32
3-4-Dihydroxybenzoic acid (5.00 g, 32.4 mmol), was dissolved in pyridine (15 mL) at 0 °C. Acetic anhydride (6.56 mL, 69.5 mmol) was added dropwise with stirring. The mixture was stirred in an ice bath for 2 h before being poured into ice water (500 mL). The precipitate was collected and purified by short column chromatography providing 12 as a yellow oil (7.50 g, 95%); νmax (KBr disc, cm-1) 1713 (CO); δH (400 MHz, DMSO-d6) 8.58 (v br, 1H, OH), 7.99 (dd, 1H, J 8.5, 2.1 Hz, H-6), 7.88 (d, 2H, J 2.1 Hz, H-2), 7.40 (d, 1H, J 8.5 Hz, H-5), 2.321, 2.318 (2× s, 2× 3H, 2× OAc); δC (100.6 MHz, DMSO-d6) 168.1, 167.8, 165.9, 149.5, 145.5, 141.9, 129.3, 127.6, 124.6, 123.8, 20.3; m/z (ESI-) 237 [M-H]-.
References:
Zhang, Qingzhi;Raheem, K. Saki;Botting, Nigel P.;Slawin, Alexandra M.Z.;Kay, Colin D.;O'Hagan, David [Tetrahedron,2012,vol. 68,# 22,p. 4194 - 4201] Location in patent:experimental part
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