Hydrochloric Acid → alpha-Methyl-2-pyridinemethanol

HRID 1659132Notes

Reaction equation

HRID 1659132 reaction equation
[BH4-].[Na+].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:5].Cl.[OH-].[Na+]>C(O)(=O)C.CO>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:4]([OH:5])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 142862-AcetylpyridineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 86784alpha-Methyl-2-pyridinemethanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

To a solution of 110 g. of sodium borohydride in 1250 ml. of methanol at 0°C. is added 350 g. of 2-pyridyl methyl ketone in 300 ml. of methanol with stirring. After stirring for 4 hours at 0°-5°C., glacial acetic acid is cautiously added dropwise, followed by ice and concentrated hydrochloric acid. The acidic solution is made basic with aqueous sodium hydroxide and extracted with dichloromethane. The organic layer is dried over magnesium sulfate, concentrated and distilled to give 1-(2-pyridyl)ethanol.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-ede7ae9551374296888bd548a529ffb6
Source dataset
uspto-grants-1976_06
Patent number
US03966945

Reaction notes

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