Sodium borohydride → 4,4,4-Trinitro-1-butanol

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Reaction Steps

Crude 4,4,4-trinitrobutaldehyde (878 g, 4.24 mol) was dissolved in methanol (1000 ml) and cooled in an ice bath while NaBH4 (130.7 g, 3.44 mol) was added portion-wise. The mixture was stirred at room temperature overnight under a nitrogen purge which removed much of the solvent. The thick suspension was hydrolyzed with 6 N HCl (approx. 41) and the product extracted with CH2Cl2 (3×1000 ml). The extracts were washed with water (1000 ml), saturated NaHCO3 (2×1000 ml), and water (1000 ml). The product solution was dried over anhydrous MgSO4 and concentrated to yield 554 g (63%) of a yellow oil, nD =4735 (19C). The infrared spectrum showed peaks at 3619, 3370, 2950, 2890, 1595, 1305, 1058 and 801 cm-1.

Provenance & Evidence