Hydrochloric Acid → Pentanol, 4-methyl-4-nitro-

Participants

Reaction Conditions

Reaction Steps

Methyl 4-methyl-4-nitropentanoate (15.5 g, 96.1 mmol) was added to a 1 L round bottomed flask, dissolved into denatured ethanol (300 ml) and cooled in an ice bath for 15 min. Sodium borohydride (7.27 g, 2 equiv, 190 mmol) was added in one portion. Hydrogen was liberated and slowly subsided. The reaction was stirred at 0° C. for 1 h then placed into a 70° C. water bath for 3 h. Water (150 ml) was poured into the flask and 6 N HCl (25 mL) was added dropwise to adjust the pH˜3 while cooled in an ice bath. The ethanol was removed under reduced pressure to give a suspension. Water (150 mL) and EA (300 mL) were added to the flask and the mixture poured into a separatory funnel. The layers were separated and the organic layer was washed with brine (100 mL), dried over anhydrous MgSO4, filtered and concentrated on a rotovap to give a pale yellow oil (12.0 g, 85.1%). 1H NMR (CDCl3, 400 MHz): ±1.5 (m, 2H), 1.61 (s, 6H), 1.95-2.05 (m, 2H), 3.65 (t, 2H). LRMS (ESI+) for C6H13NO3 (147.1); Found: 148 (MH+).

Provenance & Evidence