1-Butanol → 2,2-Dibutoxypropane

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2-dimethoxypropane (31.2 g, 0.3M), n-butanol (48.9 g, 0.66M) and toluene-p-sulphonic acid (0.05 g) is heated at 110° C., removing a fraction boiling below 60° C. over 2 hours. The mixture is cooled, brought to pH 9 with sodium methoxide in methanol, then distilled to give acetone di-n-butylketal b.p. 80° C./15 mm Hg, (33.8 g 60%). A sample of this ketal (18.8 g 0.1 m) and hypophosphorous acid (2.2 g, 0.033M) are stirred at room temperature for 7 days. Fractional distillation gives n-butyl (1-hydroxy-1-methylethyl)phosphinate (b.p. 84° C./0.3 mm Hg).

Provenance & Evidence