Hydrogen Peroxide → 2,2-Dicyclopropylethan-1-ol

HRID 1589586Notes

Reaction equation

HRID 1589586 reaction equation
[CH:1]1([CH:4]=[CH:5][CH:6]2[CH2:8][CH2:7]2)[CH2:3]C1.B.[O:10]1CCC[CH2:11]1.[OH-].[Na+].OO.[Cl-].[Na+]>O1CCCC1>[CH:6]1([CH:5]([CH:4]2[CH2:1][CH2:3]2)[CH2:11][OH:10])[CH2:7][CH2:8]1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 139135Dicyclopropyl ethyleneHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 107018422,2-Dicyclopropylethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dicyclopropyl ethylene (19 g, 0.176 mole) was dissolved in dry tetrahydrofuran (100 ml) in a three-neck flask under nitrogen and treated with borane-tetrahydrofuran in tetrahydrofuran (1M, 210 ml). The mixture was stirred at room temperature for 4 hours before adding cautiously (foaming occurs) 3N sodium hydroxide (60 ml). After addition was complete, aqueous hydrogen peroxide (30%, 60 ml) was added dropwise at a rate sufficient to maintain reflux. When addition was complete, the mixture was refluxed for a further 30 minutes, cooled and the aqueous layer saturated with sodium chloride. The layers were separated, the organic layer dried (MgSO4) and evaporated under reduced pressure to give a quantitative yield of 2,2-dicyclopropylethanol which was pure by GC. (The product could also be distilled, b.p. 99° C./25 mm.)

Workup

  1. additionAfter addition
  2. temperatureto maintain
  3. temperaturereflux
  4. additionWhen addition
  5. temperaturethe mixture was refluxed for a further 30 minutes
  6. temperaturecooled
  7. customThe layers were separated
  8. dry with materialthe organic layer dried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e846f2accc2c48c5ba56cbb6ac15c3aa
Source dataset
uspto-grants-1986_02
Patent number
US04571345

Reaction notes

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