CO.[OH-].[Na+].C[O:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]#[C:17][CH:18]2[CH2:20][CH2:19]2)=[CH:10][CH:9]=1.Cl>O.C(OCC)(=O)C.O1CCOCC1>[CH:18]1([C:17]#[C:16][C:15]#[C:14][C:11]2[CH:10]=[CH:9][C:8]([C:7]([OH:21])=[O:6])=[CH:13][CH:12]=2)[CH2:20][CH2:19]1Methanol (3.0 mL), 1,4-dioxane (3.0 mL), and a 20% aqueous solution (1.5 mL) of sodium hydroxide were added to 4-(4-cyclopropylbuta-1,3-diyn-1-yl)benzoic acid methyl ester (0.31 g) as obtained in Example 6-(1), whereafter the mixture was stirred for 2.5 hours at room temperature. Ethyl acetate and water were added, and the mixture was adjusted to pH 3 with 6 mol/L of hydrochloric acid to isolate the organic layer. The extract was dried over anhydrous magnesium sulfate, and then the desiccant was filtered out. The solvent was distilled off under reduced pressure to obtain 4-(4-cyclopropylbuta-1,3-diyn-1-yl)benzoic acid (dark brown solid) (0.28 g, 94%).
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