Sodium Hydroxide → 8-(2-Carboxy-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid
Reaction equation
C([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH2:14][C:13]2[C:8](=[C:9]([O:21][CH3:22])[C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[C:12]=2[O:15][CH3:16])[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:7][C:8]2[C:13](=[C:12]([O:15][CH3:16])[C:11]([O:17][CH3:18])=[C:10]([O:19][CH3:20])[C:9]=2[O:21][CH3:22])[CH2:14]1)([OH:5])=[O:3]Participants
4
Procedure
A mixture comprised of an ethanol (4 ml) solution of ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate (200 mg, 0.416 mmols) and an aqueous sodium hydroxide solution (3 M, 0.553 ml, 1.66 mmols) was heated under reflux for 12 hours. The reaction mixture was concentrated in vacuo, which was made acidic with 1 N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=1:2 to ethyl acetate only) to obtain the entitled compound (88.6 mg) as an oil.