1-Butanol → Butane, 1,1'-[(1-methylethylidene)bis(oxy)]bis-

HRID 1938778Notes

Reaction equation

HRID 1938778 reaction equation
[CH3:1][O:2][C:3]([O:6][CH3:7])([CH3:5])[CH3:4].[C:8]1(C)[CH:13]=CC(S(O)(=O)=O)=C[CH:9]=1.[CH2:19](O)[CH2:20][CH2:21]C>>[CH2:1]([O:2][C:3]([O:6][CH2:7][CH2:19][CH2:20][CH3:21])([CH3:5])[CH3:4])[CH2:9][CH2:8][CH3:13]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 6101p-Toluenesulfonic acidHCID 64952,2-Dimethoxypropane

Product 1

HCID 67335Butane, 1,1'-[(1-methylethylidene)bis(oxy)]bis-

Conditions

Temperature
110 °C

Procedure

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).

Workup

  1. customremoving a fraction
  2. temperatureThe mixture is cooled
  3. distillationdistilled

Sources & evidence

ORD record
ord-745efbcce4dc488d88702e9feadb468f
Source dataset
uspto-grants-1997_12
Patent number
US05693799

Reaction notes

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