Acetic Anhydride → (E)-2-Nonenyl acetate

HRID 1657951Notes

Reaction equation

HRID 1657951 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>[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

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 53649412-Nonen-1-ol, (2E)-

Product 1

HCID 6365451(E)-2-Nonenyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Pyridine (100 ml) and trans-2-nonen-1-ol (28.4 g, 0.2 mole) are heated to 110°C and acetic anhydride (30.6 g, 0.3 mole) is added dropwise. The reaction mixture is maintained at 110°-115° for 2 hours and 120°-125°C for 3 hours. The mixture is cooled and washed with water, 5% sulfuric acid, and finally water. The solution is dried over sodium sulfate. Trans-2-nonenyl acetate, 33.0 g is obtained by vacuum distillation, b.p. 70°-5°C/50-55 mm.

Workup

  1. temperatureThe reaction mixture is maintained at 110°-115° for 2 hours and 120°-125°C for 3 hours
  2. temperatureThe mixture is cooled
  3. washwashed with water, 5% sulfuric acid, and finally water
  4. dry with materialThe solution is dried over sodium sulfate

Sources & evidence

ORD record
ord-fa7ae8c18f9e426b866a3b15226286cc
Source dataset
uspto-grants-1976_06
Patent number
US03962321

Reaction notes

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