Sodium Cyanide → 12-Hydroxydodecanenitrile

HRID 1278385Notes

Reaction equation

HRID 1278385 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[C-:14]#[N:15].[Na+]>CN(C)C=O>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:14]#[N:15]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 7416311-Bromo-1-undecanol

Product 1

HCID 1033034812-Hydroxydodecanenitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution 4.6 g. of 11-bromoundecanol and 1.6 g. of sodium cyanide in 40 ml. of dimethylformamide is heated at 80° C. for 18 hours, cooled, and poured into ice-water. The mixture is extracted with methylene chloride and the extract is dried over anhydrous magnesium sulfate. Evaporation of the solution affords 12-hydroxydodecanonitrile as a yellow oil.

Workup

  1. temperaturecooled
  2. extractionThe mixture is extracted with methylene chloride
  3. dry with materialthe extract is dried over anhydrous magnesium sulfate
  4. customEvaporation of the solution

Sources & evidence

ORD record
ord-1d9be8fa42bd4aa28b64c51da6d1f1bc
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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