Methanol → 3,4-Dichloro-2-(hydroxymethyl)pyridine

HRID 1655207Notes

Reaction equation

HRID 1655207 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:14]([CH3:20])=[N:15][CH:16]=[CH:17][C:18]=1[Cl:19].FC(F)(F)C(OC(=O)C(F)(F)F)=O.CO>ClCCl>[Cl:12][C:13]1[C:14]([CH2:20][OH:9])=[N:15][CH:16]=[CH:17][C:18]=1[Cl:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 70297m-Chloroperbenzoic acidHCID 219228903,4-Dichloro-2-methylpyridine

Product 1

HCID 221173013,4-Dichloro-2-(hydroxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperbenzoic acid (32.63 g) in dichloromethane (400 ml) was added dropwise to a solution of 3,4 -dichloro-2 -picoline (25.53 g)in dichloromethane (100 ml) maintaining the temperature at 20°-25°. After standing for 16 hours at room temperature the solution was washed with 1 N NAOH, dried (K2CO3 ) and filtered to give a pale yellow solution. Trifluoroacetic anhydride (30 ml) was added dropwise to this solution maintaining the temperature at 15°-20°. After standing for 2 days at room temperature, methanol (100 ml) was added and the solution evaporated under reduced presure. The residue was treated with aqueous sodium carbonate and extracted into dichloromethane. After drying (K2CO3 ) and removal of solvent, the residue was recrystallised from pet. ether (60/80 ) to give 3,4 -dichloro-2 -hydroxymethylpyridine, 15.76 g, m.p. 66°-8°.

Workup

  1. temperaturemaintaining the temperature at 20°-25°
  2. washthe solution was washed with 1 N NAOH
  3. dry with materialdried (K2CO3 )
  4. filtrationfiltered
  5. customto give a pale yellow solution
  6. temperaturemaintaining the temperature at 15°-20°
  7. waitAfter standing for 2 days at room temperature
  8. customthe solution evaporated under reduced presure
  9. additionThe residue was treated with aqueous sodium carbonate
  10. extractionextracted into dichloromethane
  11. customAfter drying
  12. custom(K2CO3 ) and removal of solvent
  13. customthe residue was recrystallised from pet. ether (60/80 )

Sources & evidence

ORD record
ord-080221254b7f41feb105af8a698e71e2
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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