Hydrochloric Acid → HCID 68469329, compound

HRID 1623598Notes

Reaction equation

HRID 1623598 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:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>O.C1(C)C=CC=CC=1>[CH2:13]([O:23][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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81741-DecanolHCID 14798Sodium HydroxideHCID 98774464-Chloro-2,3-dimethyl-1-oxidopyridin-1-ium

Product 1

HCID 68469329HCID 68469329, compoundYield 151%

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 28.5 g of 1-decanol (0.18 mol, 1.8 eq.) were added to 64 mL of toluene, and the mixture was heated to reflux for 4 hours, and then cooled to room temperature. 160 mL of water was added to the reaction liquid, and then the mixture was neutralized with concentrated hydrochloric acid (7.3 g). Subsequently, the resultant was extracted with 100 mL of ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure, to obtain 42.2 g of 4-decyloxy-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 with 100 mL of ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-36a7a94dab174b1daf787947a5ee21d3
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

Loading…