Oxalic Acid → HCID 5282919, compound

Reaction equation

[Li+].[OH-].[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]C)=[O:24].C(O)(=O)C(O)=O>C1COCC1.O>[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

Procedure

LiOH (45 μL of a 1 M aqueous soln) was added to a stirring, room temperature solution of the above ester (5.2 mg, 0.015 mmol) in THF/H2O (5:1, 1.5 mL). After 10 hours, the pH was adjusted to 4 using 1 M oxalic acid and the reaction mixture was extracted with EtOAc (3×4 mL). The combined organic extracts were evaporated in vacuo to give 20-hydroxyeicosanoic acid (55) (4.5 mg, 92%) as a solid, mp 86° C. 1H NMR (250 MHz, CD3OD): δ 1.20-1.45 (m, 30H), 1.45-1.63 (m, 4H), 2.28 (t, J˜7.4 Hz, 2H), 3.55 (t, J˜6.5 Hz, 2H); TLC: EtOAc/hexanes (3:7), Rf˜0.08. 19-Hydroxynonadecanoic Acid (56) was prepared in an analogous manner from ester 8a.