Hydrogen Cyanide → Hexanamide, 2-hydroxy-

HRID 967349Notes

Reaction equation

HRID 967349 reaction equation
S(=O)(=O)(O)[OH:2].[CH2:6]([CH:10]([OH:13])[C:11]#[N:12])[CH2:7][CH2:8][CH3:9].C#N>O>[OH:13][CH:10]([CH2:6][CH2:7][CH2:8][CH3:9])[C:11]([NH2:12])=[O:2]

Participants

5

Reactant 3

HCID 768Hydrogen Cyanide2×HCID 1118Sulfuric Acid2×HCID 124520212-Hydroxyhexanenitrile

Product 1

HCID 9833961Hexanamide, 2-hydroxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirrer, a thermometer and a dropping funnel were set to a 1,000-mL four-necked flask and to a reaction apparatus, 95% sulfuric acid (450 g, 4.4 mol) was added and cooled so that the liquid temperature was lower than 30° C. To the cooled sulfuric acid with stirring, was added α-n-butyl-α-hydroxyacetonitrile prepared from n-butyl aldehyde and hydrocyanic acid (1.5 mol, content 87 to 94%, further containing unreacted hydrocyanic acid, starting material n-butyl aldehyde and water) with the use of dropping funnel. The addition was conducted in such a way that the reaction solution was kept at a temperature of lower than 40° C. After the dropwise addition, the reaction solution was aged at 40° C. for 0.5 hr. The pH of the reaction solution was less than 1. A part of the reaction solution was sampled and analyzed by HPLC. In result, the ratio of conversion of the starting materials was 100% and the corresponding 2-hydroxyhexanoic acid amide and 2-hydroxysulfonyl oxy hexanoic acid amide were produced.

Workup

  1. additionwas added
  2. temperaturecooled so that the liquid temperature
  3. customwas lower than 30° C
  4. additionThe addition
  5. customlower than 40° C
  6. additionAfter the dropwise addition
  7. aliquotA part of the reaction solution was sampled
  8. customIn result

Sources & evidence

ORD record
ord-825477f67740480a9d502f7b6c36f0d8
Source dataset
uspto-grants-2005_10
Patent number
US06953859B2

Reaction notes

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