C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:17][OH:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O1CCCC1.C(OCC)C.O>[OH:18][CH2:17][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:19])=[O:2])=[CH:9][CH:8]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]
4-(1-Hydroxymethyl-heptyl)-benzoic acid methyl ester (3.46 g, 12.1 mmol) is dissolved in tetrahydrofuran (40 mL) and 5N sodium hydroxide (10 mL) is added. The reaction may be monitored by HPLC and is complete within 8 h. The reaction is neutralized with 5N HCl (10 mL), and diluted with diethyl ether and water. The two phases are separated, and the organic layer is washed, dried, and concentrated to provide the title compound which is used without further purification. MS (ES): 249.3 [M+H]−.
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