2-Methyl-1-pentanol → HCID 118384826, compound

Participants

Reaction Conditions

Reaction Steps

Octadecanedioic acid (ODDA, 5.00 g) was added to a 100-mL three-necked round-bottom flask. A Dean-Stark condenser was attached, followed by the addition of toluene to the ODDA and to the trap. 2-Methylpentyl alcohol (5.90 mL) was added to the ODDA mixture. The flask was immediately purged with nitrogen gas and p-toluenesulfonic acid (0.17 g) was added. The reaction mixture was heated to 115° C. and the reaction proceeded for 5 hours. Heat was then removed and the reaction mixture was allowed to cool to 60° C., at which point aqueous NaHCO3 (saturated) was added to achieve a neutral pH. After vigorous stirring, the organic layer was separated and dried over Na2SO4. The dried product was then subjected to a vacuum treatment to remove any residual solvent. A yellow oil was obtained. Analysis by 1H NMR provided the following chemical shifts: (400 MHz, CDCl3) δ 0.90-0.85 (m), 1.10-1.20 (m), 1.21-1.50 (m), 1.55-1.7 (t), 1.77 (o), 2.30 (t), 3.85 (dd), 3.95 (dd). Anaylsis by 13C NMR provided the following chemical shifts: (400 MHz, CDCl3) δ C, 173.947; CH, 32.366; CH2, 69.200, 35.691, 34.438, 29.701, 29.684, 29.641, 29.516, 29.319, 29.220, 25.095, 19.975; CH3, 16.885, 14.258.

Provenance & Evidence