Yield:27741-01-1 90%

Reaction Conditions:

with lithium hydroxide in methanol at 50;

Steps:

4.1.1 Synthesis of geniposidic acid (1)
Geniposide (3g, 0.00773mol) was dissolved in methanol (25mL) and hydrolyzed with 2M LiOH solution (8mL, 0.01546mol) at 50°C overnight. Then 1N hydrochloric acid solution (10mL) was added by drops until the PH became a weak acid. The reaction solution was concentrated under reduced pressure to afford a light brown solid (compound 1) in 90% yield. ¹H NMR (400MHz, CD₃OD): δ 7.43 (s, 1H), 5.64 (br. s., 1H), 5.08 (d, J=6.65Hz, 1H), 5.02 (d, J=5.09Hz, 1H), 4.95 (d, J=5.09Hz, 1H), 4.92 (d, J=5.48Hz, 1H), 4.70 (t, J=5.48Hz, 1H), 4.49 (d, J=7.83Hz, 1H), 4.44 (t, J=5.87Hz, 1H), 4.08 (br. s., 1H), 3.90-4.02 (m, 3H), 3.34-3.42 (m, 1H), 2.91-3.16 (m, 6H), 2.57-2.70 (m, 2H), 2.45-2.48 (m, 1H).

References:

Lei, Shuwen;Zhang, Dongdong;Qi, Yunyue;Chowdhury, Sharmin Reza;Sun, Ran;Wang, Juntao;Du, Yi;Fu, Lei;Jiang, Faqin [European Journal of Medicinal Chemistry,2020,vol. 205,art. no. 112508]

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