Formaldehyde → 2-Methyl-2-nitrobutan-1-ol

Temperature

40 °C

A 2-liter 3-neck flask is equipped with a mechanical stirrer, a reflux condenser with a nitrogen bubbler, an addition funnel and a temperature controller with heating mantle and thermocouple. The flask is charged with aqueous formaldehyde solution (420 mL, 37% active, 5.64 mol) and 4 mL triethylamine catalyst. The addition funnel is charged with 2-nitrobutane (554.1 g, 5.37 mol). The 2-nitrobutane is added dropwise, over a period of 7 hours to the formaldehyde solution, which is being stirred under nitrogen. The reaction is maintained at 40° C. during the addition. After all the 2-nitrobutane is added, the turbid mixture is warmed to 45° C. for 30 min, and then heating and stirring are discontinued overnight. If a GC analysis indicates the reaction is not yet complete; an additional 10.9 g aqueous formaldehyde is added and the mixture stirred at 45° C. for 2.5 hours. Upon cooling to room temperature, the reaction mass separates into an oil layer with a smaller, separate water layer. The oil layer is collected (1022.8 g, 97.9% of theory) and GC indicates 94.8% purity. The oil is used without further purification.

1. customA 2-liter 3-neck flask is equipped with a mechanical stirrer, a reflux condenser with a nitrogen bubbler, an addition funnel
2. temperaturea temperature controller with heating mantle and thermocouple
3. temperaturethe turbid mixture is warmed to 45° C. for 30 min
4. temperatureheating
5. stirringstirring
6. stirringthe mixture stirred at 45° C. for 2.5 hours
7. temperatureUpon cooling to room temperature
8. customseparate water layer
9. customThe oil layer is collected (1022.8 g, 97.9% of theory) and GC
10. customThe oil is used without further purification

ORD record

ord-3a34afe5c0954ab6908d108a5919fb77

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187436B2