1,4-Dioxane → 4-Hydroxymethyl-2,6-di-t-butylpyridine

HRID 1861891Notes

Reaction equation

HRID 1861891 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[N:6]=[C:5]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=1.[O:17]1CCOCC1>[OH-].[Na+].O>[OH:17][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[N:6]=[C:5]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=1

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 129308884-(Bromomethyl)-2,6-di-tert-butylpyridine2×

Product 1

HCID 129668344-Hydroxymethyl-2,6-di-t-butylpyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A heterogeneous solution of 4-bromomethyl-2,6-di-t-butylpyridine (Compound A3, 1.743 g, 82% purity) in 20 ml of 12% NaOH in water and 10 ml of 1,4-dioxane was refluxed for 12 hours. The solution spontaneously separated into two layers as it cooled to room temperature. The upper layer was separated and ethyl acetate was added. This organic layer was then washed with brine, water and dried over MgSO4. The desired product was purified by column chromatography (ethyl acetate/hexane 1/9) to give a white solid. 1H NMR δ 7.09 (s, 2H), 4.67 (d, J=4.4 Hz, 2H), 2.3 (b, 1H), 1.36 (s, 18H).

Workup

  1. customThe solution spontaneously separated into two layers as it
  2. customThe upper layer was separated
  3. additionethyl acetate was added
  4. washThis organic layer was then washed with brine, water
  5. dry with materialdried over MgSO4
  6. customThe desired product was purified by column chromatography (ethyl acetate/hexane 1/9)
  7. customto give a white solid

Sources & evidence

ORD record
ord-100cc83a9cfa4f6c84212ba39d11e2ae
Source dataset
uspto-grants-2003_03
Patent number
US06534544B1

Reaction notes

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