Pyridine → (Z)-Non-2-enyl acetate

HRID 1657947Notes

Reaction equation

HRID 1657947 reaction equation
[CH2:1]([OH:10])/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:11](OC(=O)C)(=[O:13])[CH3:12].N1C=CC=CC=1>O>[C:11]([O:10][CH2:1]/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 53650272-Nonen-1-ol, (2Z)-

Product 1

HCID 20836153(Z)-Non-2-enyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cis-2-nonenol (2.9 g, 0.03 mole), acetic anhydride (3.1 g, 0.045 mole) and pyridine (15 ml) is heated at reflux for 3 hours. The solution is cooled and diluted with water. The organic layer is separated and washed successively with 3% sulfuric acid, and water. The solution is dried over sodium sulfate and distilled under vacuum to yield cis-2-nonenyl acetate, b.p. 58° - 62°C/0.1 mm.

Workup

  1. temperatureat reflux for 3 hours
  2. temperatureThe solution is cooled
  3. customThe organic layer is separated
  4. washwashed successively with 3% sulfuric acid, and water
  5. dry with materialThe solution is dried over sodium sulfate
  6. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-82dad48362814c0a92365c2717628692
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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