Sodium Hydroxide → 4-(4-Methanesulfonylphenoxymethyl)-2,6-dimethylpyridine

HRID 1788364Notes

Reaction equation

HRID 1788364 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([CH3:11])[CH:5]=1.[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[OH-].[Na+]>C(O)C>[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:3][C:4]2[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([CH3:11])[CH:5]=2)=[CH:18][CH:17]=1)(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1233504-(Methylsulfonyl)phenolHCID 230016454-(Chloromethyl)-2,6-dimethylpyridine hydrochloride

Product 1

HCID 230179774-(4-Methanesulfonylphenoxymethyl)-2,6-dimethylpyridineYield 46.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.0 g (5.21 mmol) of 4-chloromethyl-2,6-dimethylpyridine hydrochloride and 1.1 g (6.25 mmol) of 4-methylsulfonylphenol in ethanol (3.5 mL) was added 3.5 mL (14.0 mmol) of 4 N aqueous sodium hydroxide solution, followed by heating under reflux for 90 minutes. After standing to cool, ethanol was evaporated under a reduced pressure. To the obtained residue, water was added and the precipitates were collected by filtration and then dried under a reduced pressure to obtain 707 mg (yield 46.6%) of 4-(4-methanesulfonylphenoxymethyl)-2,6-dimethylpyridine (VI-4) as a colorless crystal. Its physical property is shown below.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 90 minutes
  3. temperatureto cool
  4. customethanol was evaporated under a reduced pressure
  5. additionTo the obtained residue, water was added
  6. filtrationthe precipitates were collected by filtration
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-c339712575dd4559b93b4a15ca21bf5f
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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