Water → Trioctylborane

HRID 865824Notes

Reaction equation

HRID 865824 reaction equation
COCCS[CH2:6][CH2:7]OC.[BH3:10].[CH2:11]=[CH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>ClCCl>[CH2:11]([B:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:6][CH3:7])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 81251-OcteneHCID 178419212HCID 178419212, compound

Product 1

HCID 11142667Trioctylborane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Borane bis(2-methoxyethyl) sulfide (5.0 ml, 30 mmol) was dissolved in dichloromethane (30 ml) and 1-octene (10.10 g, 90 mmol) was added dropwise with cooling to keep the temperature at 20°-25° C. The reaction was complete in 5 min as indicated by 11B NMR. The solution was vigorously stirred with water (10×20 ml), dried over magnesium sulfate and the solvent was removed under vacuum. 1H NMR spectrum showed the sulfide present. Diethyl ether (20 ml) was added, followed by 5% sodium hypochlorite solution (40 ml) and the mixture was stirred keeping the temperature at 20°-25° C. After 1 h, the organic phase was separated, washed with water (3×20 ml) and dried over magnesium sulfate. Ether was removed under vacuum to give trioctylborane, 9.84 g, 94%, 11B NMR, δ, 86 ppm. 1H NMR did not indicate bis(2-methoxyethyl)sulfide. Tetrahydrofuran (30 ml) was added, followed by 3M sodium hydroxide (10 ml, 30 mmol) and 30% hydrogen peroxide (10 ml, 100 mmol). The mixture was stirred for 2 h at room temperature and then 1 hour at 40° C., saturated with potassium carbonate, the organic layer was separated and the aqueous layer was extracted with diethyl ether (2×30 ml). The extracts were combined with the THF solution, dried over magnesium sulfate and octanol was isolated by distillation, 10.60 g, 90.5%, bp 99°-100° C./20 mm Hg. GC analysis (Carbowax 20 M) showed 1-octanol (94%) and 2-octanol (6%).

Workup

  1. temperaturewith cooling
  2. customat 20°-25° C
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was removed under vacuum
  5. additionDiethyl ether (20 ml) was added
  6. customat 20°-25° C
  7. waitAfter 1 h
  8. customthe organic phase was separated
  9. washwashed with water (3×20 ml)
  10. dry with materialdried over magnesium sulfate
  11. customEther was removed under vacuum

Sources & evidence

ORD record
ord-97d1d225758a418695a2d8bc2372aa2a
Source dataset
uspto-grants-1996_10
Patent number
US05567849

Reaction notes

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