Hydrochloric Acid → HCID 68466272, compound

HRID 1623587Notes

Reaction equation

HRID 1623587 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N+:5]([O-:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[OH-].[Na+].[CH2:13]([OH:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Cl>O.C1(C)C=CC=CC=1>[CH2:13]([O:19][C:2]1[CH:7]=[CH:6][N+:5]([O-:8])=[C:4]([CH3:9])[C:3]=1[CH3:10])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81031-HexanolHCID 14798Sodium HydroxideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 68466272HCID 68466272, compoundYield 148.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

15.8 g (0.1 mol, 1.0 eq.) of 4-chlor-2,3-dimethylpyridine-N-oxide, 8.0 g (0.2 mol, 2.0 eq.) of caustic soda, and 20.4 g (0.2 mol, 2.0 eq.) of 1-hexanol were added to 64 mL of toluene, and the mixture was heated to reflux for 4 hours, and then cooled to room temperature. 15 mL of water was added to the reaction liquid, and then the mixture was neutralized with concentrated hydrochloric acid (8 mL). Subsequently, the resultant was extracted three times with 670 mL of chloroform. The extract was dried over anhydrous magnesium sulfate, and then concentrated to dryness, to obtain 33.1 g of 4-hexyloxy-2,3-dimethylpyridine-N-oxide as a black brown oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. extractionSubsequently, the resultant was extracted three times with 670 mL of chloroform
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0153f711a9d246a88ebfe86a5b4074ef
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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