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

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Reaction Conditions

Reaction Steps

50 g (0.285 mol) methyl 4-methyl-4-nitro-pentanoate are dissolved in a 6:4 mixture of THF/ethanol (1000 mL). The solution is cooled to −10° C. and combined with 24.2 g (0.571 mol) lithium chloride. Then 21.6 g (0.571 mol) lithium borohydride are added batchwise. The mixture is stirred for 30 minutes at −10° C. and then heated overnight to ambient temperature. The reaction mixture is stirred for 6 hours at 60° C. and overnight at ambient temperature. It is combined with water and adjusted to pH 6 with dilute hydrochloric acid. The solvent is distilled off and the residue is combined with water. The mixture is extracted with dichloromethane, the combined organic phases are washed with water and ammonium chloride solution and dried with sodium sulphate. After elimination of the solvent the product is obtained as a yellow oil.

Provenance & Evidence