Acetone → HCID 10953608, compound

HRID 407188Notes

Reaction equation

HRID 407188 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[N-:8]=[N+:9]=[N-:10].[Na+].CC(C)=O>O>[N:8]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[OH:7])=[N+:9]=[N-:10]

Participants

5

Reactant 3

HCID 180AcetoneHCID 9246Cyclohexene oxideHCID 33557Sodium Azide

Product 1

HCID 10953608HCID 10953608, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A solution of cyclohexene oxide (10.1 g, 103 mmol) and sodium azide (16.7 g, 257 mmol) in 100 mL of a 1:1 mixture of acetone:water was heated to reflux at 75° C. for 14 h. The mixture was cooled to rt, concentrated in vacuo to 50 mL, and extracted 3× with dichloromethane. The combined organic fractions were washed 2× with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-azidocyclohexanol that gave a proton NMR spectra consistent with theory.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated in vacuo to 50 mL
  3. extractionextracted 3× with dichloromethane
  4. washThe combined organic fractions were washed 2× with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e66369b1cc654ac4aa03ce335a60c17c
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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