Formaldehyde → 2-Nitro-2-isopropyl-1,3-propanediol

A solution of 2-methyl-1-nitropropane (38.7 g, 0.375 mol prepared by the procedure of N. Kornblum, B. Taube, and H. Ungnade, J. Am. Chem. Soc. 76, 3209 (1954) and NEt3 (Eastman 3.79 g, 0.0375 mol) in CH3OH (50 mL) was added dropwise 37% aqueous formaldehyde solution (Mallinckrodt, 76.2 g, 0.938 mol), at a rate such that the reaction mixture temperature did not exceed 30°. After 72 h, the solution was concentrated under vacuum and the residue was dissolved in H2O (250 mL). The solution was continuously extracted for 1 h with CH2Cl2 (1 L). The CH2Cl2 solution was dried (MgSO4), filtered, and concentrated to give 53.3 g (87%) of 2-isopropyl-2-nitro-1,3-propanediol a waxy, white solid mp 67°-72° (lit. mp 87°-88°, B. M. Vanderbilt and H. B. Hass, Ind. Eng. Chem. 32, 34 (1940). In our hands this procedure failed to give the desired compound).

1. customdid not exceed 30°
2. concentrationthe solution was concentrated under vacuum
3. dissolutionthe residue was dissolved in H2O (250 mL)
4. extractionThe solution was continuously extracted for 1 h with CH2Cl2 (1 L)
5. dry with materialThe CH2Cl2 solution was dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-31007e54c34542028da9e5b878618459

Source dataset

uspto-grants-1989_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04808625