Acetic Anhydride → (6-Methylpyridin-3-yl)methyl acetate

HRID 464076Notes

Reaction equation

HRID 464076 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][N:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10](=[O:12])[CH3:11])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 20263926(6-Methylpyridin-3-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methyl-5-hydroxymethylpyridine (0.1 mole) is stirred in pyridine (50 ml.) with acetic anhydride (0.15 mole) at room temperature overnight. The mixture is concentrated to dryness, and the residue is dissolved in 70 ml. of water and extracted with 3×25 ml. of chloroform. After drying over magnesium sulfate, the chloroform is concentrated to dryness to give 2-methyl-5-acetoxymethylpyridine.

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. dissolutionthe residue is dissolved in 70 ml
  3. extractionof water and extracted with 3×25 ml
  4. dry with materialAfter drying over magnesium sulfate
  5. concentrationthe chloroform is concentrated to dryness

Sources & evidence

ORD record
ord-6f1653505b5e4119a51a2fed3cddc2a1
Source dataset
uspto-grants-1985_10
Patent number
US04546106

Reaction notes

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