Hydrochloric Acid → HCID 70432418, compound

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Reaction Steps

To a solution of methyl 4-[(E)-1-tridecenyl]cinnamate (342 mg, 1 mmole from Example 16 in 50% aqueous tetrahydrofuran (25 ml) was added lithium hydroxide monohydrate (420 mg, 10 equivalents) and the mixture was stirred at room temperature overnight. The cloudy mixture was acidified with dilute hydrochloric acid and extracted with ether. The extracts were washed with brine, dried (magnesium sulphate) and evaporated to a white crystalline solid. Yield 330 mg (100%). Recrystallisation from methanol afforded material of mp 107° C., νmax (mull) 2600 (broad), 1710, 1680, 1625, 1425, 1308, 1285 cm-1 ; δ(DMSO-d6) 0.82 (3H, distorted t, CH3), 1.25 (18H, m. alkylene chain), 2.18 (2H, m, allylic CH2), 6.37 (2H, distorted s), 6.48 (1H, d, J 15 Hz, C=CHCO2), 7.52 (4H, AB quartet, J 7.5 Hz, Δν 18 Hz, aromatics), 7.60 (1H, d, J 15 Hz, ArCH=C--CO2) λmax (MeOH) 307 (31,200), 226 (12,200) nm.

Provenance & Evidence