Sodium Hydroxide → 2-Hydroxymethyl-3-methyl-4-propoxy-pyridine

HRID 1623580Notes

Reaction equation

HRID 1623580 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 684689472-Acetoxymethyl-3-methyl-4-propoxy-pyridine

Product 1

HCID 140971152-Hydroxymethyl-3-methyl-4-propoxy-pyridineYield 48.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

27.8 g of 2-acetoxymethyl-3-methyl-4-propoxy-pyridine was added dropwise into a 25% aqueous solution of sodium hydroxide, and the mixture was allowed to react for one hour at room temperature. Subsequently, the reaction liquid was diluted with toluene, and then the toluene phase was washed with water, dried over anhydrous magnesium sulfate, and then concentrated to dryness, to obtain 11.0 g of 2-hydroxymethyl-3-methyl-4-propoxy-pyridine as an oily matter.

Workup

  1. customto react for one hour at room temperature
  2. customSubsequently, the reaction liquid
  3. washthe toluene phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a41668ad33484ba3acc5aa1d60f20f7e
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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