Hydrochloric Acid → alpha-Methyl-2-pyridinemethanol

HRID 1414260Notes

Reaction equation

HRID 1414260 reaction equation
[Na].[CH3:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)=[O:4].Cl.[OH-].[Na+]>C(O)(=O)C.CO>[N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:3]([OH:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 142862-AcetylpyridineHCID 14798Sodium HydroxideHCID 5360545Sodium

Product 1

HCID 86784alpha-Methyl-2-pyridinemethanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

To a solution of 110 g. of sodium borohylride 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-ada035836c6e4012980fa4b9959054dd
Source dataset
uspto-grants-1977_01
Patent number
US04001241

Reaction notes

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