[C:1]([C:14]1[CH:25]=[CH:24][C:17]([CH:18]=[CH:19][C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]To a solution of methyl 4-(1-tridecynyl)cinnamate (680 mg, 2 mmole) in tetrahydrofuran (25 ml) was added a solution of lithium hydroxide monohydrate (0.84 g) in water (25 ml) and the mixture was stirred overnight at room temperature. The cloudy mixture was acidified with dilute hydrochloric acid and then extracted with ether. The ethereal extracts were washed with brine, dried (MgSO4) and evaporated to a white crystalline solid. Yield 0.650 g (100%). Recrystallisation from methanol afforded material of mp 156°-157° C., υmax mull, 2650 (broad), 1710, 1685, 1630 cm-1, δ(DMSO), 0.85 (3H, distorted t, terminal CH3), 1.25 (18H, m, alkylene chain), ca 2.43 (2H, m, C≡C--CH2), 6.50 (1H, d, J 15.8 Hz, =CHCO2), 7.51 (4H, ABq, J 8.4 Hz, Δν22.4 Hz, arom), 7.57 (1 H, d, J 15.8 Hz, ArCH=), 12.5 (1H, broad, exchangeable, CO2H).
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