Acetic Anhydride → HCID 13154060, compound

HRID 1973902Notes

Reaction equation

HRID 1973902 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=C(C)[N+:13]([O-])=[CH:14][C:15]=1[CH2:16][CH2:17][CH2:18][CH3:19]>C1(C)C=CC=CC=1>[C:5]([O:4][CH2:1][C:2]1[CH:11]=[C:10]([O:9][CH3:8])[C:15]([CH2:16][CH2:17][CH2:18][CH3:19])=[CH:14][N:13]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13154059HCID 13154059, compound

Product 1

HCID 13154060HCID 13154060, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.4 g (0.2 mol) of acetic anhydride are added dropwise to a solution of 19.5 g (0.1 mol) of 4-methoxy-5-n-butyl-2-picoline-N-oxide in 100 ml of toluene over the course of 15 minutes, whilst stirring. Thereafter the mixture is heated for 8 hours under reflux. After evaporation to dryness in vacuo, the mixture is rendered alkaline with 2 N aqueous sodium carbonate solution and is extracted with ether. The ether phases are combined, dried with sodium sulphate, filtered and evaporated. Distillation of the residue in a bulb tube in a high vacuum at 120° yields 2-acetoxymethyl-4-methoxy-5-n-butyl-pyridine.

Workup

  1. temperatureThereafter the mixture is heated for 8 hours
  2. temperatureunder reflux
  3. customAfter evaporation to dryness in vacuo
  4. extractionis extracted with ether
  5. dry with materialdried with sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. distillationDistillation of the residue in a bulb tube in a high vacuum at 120°

Sources & evidence

ORD record
ord-e874a6d5719e4183a7c44ac338061d01
Source dataset
uspto-grants-1976_12
Patent number
US03998955

Reaction notes

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