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

HRID 1417022Notes

Reaction equation

HRID 1417022 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 A, 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-18deebdf567a4325b76328eeb219af5f
Source dataset
uspto-grants-1999_06
Patent number
US05917048

Reaction notes

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