1-Octanol → Octyl 2-pyrazinecarboxylate

HRID 1440017Notes

Reaction equation

HRID 1440017 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16](O)=[O:17]>S(=O)(=O)(O)O>[N:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:16]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:17]

Participants

4

Reactant 2

HCID 9571-OctanolHCID 10472-Pyrazinecarboxylic acid

Product 1

HCID 465427Octyl 2-pyrazinecarboxylateYield 88.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A four-necked flask was charged with 426 g (3.271 mole) of 1-octanol, 100 g (0.806 mole) of pyrazinecarboxylic acid and 5.0 g (0.05 mole) of concentrated sulfuric acid and the internal temperature was maintained under stirring at 97°-100° C. for 8 hours. The reaction mixture was then cooled and transferred to a separatory funnel, in which it was washed with two portions, or a total of 330 g, of 8% aqueous solution of sodium carbonate. The oil layer which separated was washed with water and subjected to distillation under reduced pressure to give 168 g of octyl pyrazinecarboxylate. Yield: 88% (based on pyrazinecarboxylic acid).

Workup

  1. temperaturethe internal temperature was maintained
  2. temperatureThe reaction mixture was then cooled
  3. customtransferred to a separatory funnel, in which it
  4. washwas washed with two portions
  5. customThe oil layer which separated
  6. washwas washed with water
  7. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-4f7955ab85834912a611039ed6dd0492
Source dataset
uspto-grants-1996_03
Patent number
US05496949

Reaction notes

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