Cyclohexene oxide → HCID 10953608, compound

HRID 478960Notes

Reaction equation

HRID 478960 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[Cl-].[NH4+].[N-:10]=[N+:11]=[N-:12].[Na+]>C(O)C.O>[N:10]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[OH:7])=[N+:11]=[N-:12]

Participants

6

Reactant 3

HCID 9246Cyclohexene oxideHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 10953608HCID 10953608, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of cyclohexene oxide (150 g, 1.53 mol) in a mixture of ethanol (600 ml) and water (600 ml) is added ammonium chloride (168 g, 3.1 mol) followed by sodium azide (198 g, 3 mol). The resulting solution is stirred gently at 50° C. for 12 hours before being allowed to cool. The volatiles are removed in vacuo, and 6M hydrochloric acid (˜120 ml) is added to bring the reaction to pH 7. The reaction is extracted with ethyl acetate (2×750 ml), and the organic extracts are washed with brine (750 ml) and dried over sodium sulfate. Removal of the solvent in vacuo affords 2-azido-cyclohexan-1-ol as a slightly yellow oil (171.8 g, 80%), which is used in the following step without further purification.

Workup

  1. temperatureto cool
  2. customThe volatiles are removed in vacuo, and 6M hydrochloric acid (˜120 ml)
  3. additionis added
  4. customthe reaction to pH 7
  5. extractionThe reaction is extracted with ethyl acetate (2×750 ml)
  6. washthe organic extracts are washed with brine (750 ml)
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-12d13c5339a348e6986575804d0a8365
Source dataset
uspto-grants-2003_11
Patent number
US06642390B2

Reaction notes

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