Hexane → HCID 21392667, compound

HRID 461985Notes

Reaction equation

HRID 461985 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[CH:8]([CH2:13][CH:14]=[O:15])CCCC.S(=O)(O)[O-].[Na+].[C-:21]#[N:22].[Na+]>O>[CH:3]12[CH2:1][CH:2]1[CH2:6][CH2:5][CH:4]2[CH2:8][CH2:13][CH:14]([C:21]#[N:22])[OH:15]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8929Sodium CyanideHCID 1196783-MethylheptanalHCID 23665763Sodium Bisulfite

Product 1

HCID 21392667HCID 21392667, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

0.01 Mole of exobicyclo[3.1.0]hex-2-yl acetaldehyde and 0.01 mole of sodium bisulfite are stirred in 20 ml. of water at room temperature until all of the aldehyde is dissolved. 0.02 Mole of sodium cyanide in 5 ml. of water is then added and the mixture stirred for 30 minutes at room temperature. The solution is then extracted three times with ethyl acetate and the combined ethyl acetate extract dried over anhydrous magnesium sulfate, filtered and then evaporated under vacuum to remove the solvent, yielding 1-(bicyclo[3.1.0]hex-2-yl)-3-cyano-3-hydroxypropane.

Workup

  1. extractionThe solution is then extracted three times with ethyl acetate
  2. extractionthe combined ethyl acetate extract
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. customto remove the solvent

Sources & evidence

ORD record
ord-011d36dc64c34fd8b2c9f08815dd4d3d
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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