4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium → HCID 24816049, compound

HRID 31723

Reaction equation

HRID 31723 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].[CH3:12][C:13]1([CH3:21])[O:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15][O:14]1>C1(C)C=CC=CC=1>[CH3:12][C:13]1([CH3:21])[O:18][CH2:17][CH:16]([CH2:19][O:20][C:2]2[C:7]([CH3:8])=[CH:6][N+:5]([O-:9])=[C:4]([CH3:10])[C:3]=2[CH3:11])[CH2:15][O:14]1

Participants

4

Reactant 2

HCID 27791414-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-iumHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanol

Product 1

HCID 24816049HCID 24816049, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-chloro-2,3,5-trimethylpyridine 1-oxide (840 g), (2,2-dimethyl-1,3-dioxan-5-yl)methanol (688 g) and toluene (2.52 L) was heated under reflux while removing a water content. While azeotropical dehydration was continued, potassium hydroxide (0.58 kg) was added to the reaction mixture over 3 hours and 45 minutes, and azeotropic dehydration was continued for 2.5 hours. The mixture was cooled to 30° C. or less, and ethyl acetate (2.5 L) and a 17% saline solution (3.5 L) were added to the mixture and then the mixture was allowed to stand for overnight. The ethyl acetate layer was separated and the aqueous layer was extracted with ethyl acetate (1.0 L×3). The ethyl acetate layers were combined, filtrated through celite, and concentrated under reduced pressure to obtain a desired product (1.20 kg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customwhile removing a water content
  4. additionpotassium hydroxide (0.58 kg) was added to the reaction mixture over 3 hours and 45 minutes
  5. temperatureThe mixture was cooled to 30° C. or less
  6. additionethyl acetate (2.5 L) and a 17% saline solution (3.5 L) were added to the mixture
  7. waitto stand for overnight
  8. customThe ethyl acetate layer was separated
  9. extractionthe aqueous layer was extracted with ethyl acetate (1.0 L×3)
  10. filtrationfiltrated through celite
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-54dbbcbe5d074cb09cd083371b18cc7c
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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