(4-methoxypyridin-2-yl)methyl Acetate → (4-Methoxy-pyridin-2-yl)-methanol

HRID 638586Notes

Reaction equation

HRID 638586 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][N:7]=1)(=O)C>Cl.[Hg]>[OH:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 10726082(4-methoxypyridin-2-yl)methyl Acetate

Product 1

HCID 10820596(4-Methoxy-pyridin-2-yl)-methanolYield 67%

Reagents, catalysts & solvents 2

HCID 23931MercuryCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2-acetoxymethyl-4-methoxypyridine (20.72 g, 0.114 mole) in 3M hydrochloric acid (100 ml) was heated under reflux for 1 hour. The resulting solution was concentrated under reduced pressure and the residue neutralised by addition of potassium carbonate. The mixture was extracted with dichloromethane and the organic solution dried over anhydrous sodium sulphate, filtered and evaporated to give a light coloured viscous oil which solidified on standing to yield the title compound (10.6 g, 67%) b.p. 135° C. at 0.1 mm mercury.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe resulting solution was concentrated under reduced pressure
  3. additionthe residue neutralised by addition of potassium carbonate
  4. extractionThe mixture was extracted with dichloromethane
  5. dry with materialthe organic solution dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a light

Sources & evidence

ORD record
ord-d43c60e54378460d8ad0d58a360d0b13
Source dataset
uspto-grants-1985_12
Patent number
US04562197

Reaction notes

Loading…