Hydrochloric Acid → Octyl 2-pyrazinecarboxylate

HRID 1440015Notes

Reaction equation

HRID 1440015 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].Cl>C(Cl)Cl>[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

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 9571-OctanolHCID 10472-Pyrazinecarboxylic acid

Product 1

HCID 465427Octyl 2-pyrazinecarboxylateYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A four-necked flask was charged with 100 g (0.768 mole) of 1-octanol and 10 g (0.081 mole) of pyrazinecarboxylic acid and while the internal temperature was maintained under stirring at 70°-80° C., 15 g (0.411 mole) of hydrogen chloride was introduced through a gas inlet tube over a period of 3 hours. Upon completion of the introduction of hydrogen chloride, the reaction mixture was cooled and 100 ml of methylene chloride was added. The mixture was transferred to a separatory funnel, in which it was washed with a small quantity of aqueous sodium carbonate solution. From the oil layer which separated, the methylene chloride was first distilled off and the residue was subjected to distillation under reduced pressure to give 11.5 g of octyl pyrazinecarboxylate. Yield: 60% (based on pyrazinecarboxylic acid)

Workup

  1. temperaturewas maintained
  2. customThe mixture was transferred to a separatory funnel, in which it
  3. washwas washed with a small quantity of aqueous sodium carbonate solution
  4. customFrom the oil layer which separated
  5. distillationthe methylene chloride was first distilled off
  6. distillationthe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-43ec2ccfadbe4c6ab312224d2b92f934
Source dataset
uspto-grants-1996_03
Patent number
US05496949

Reaction notes

Loading…