Sodium Hydroxide → HCID 23614955, compound

HRID 1985996Notes

Reaction equation

HRID 1985996 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[N:3]=1.[OH:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH2:25])=[CH:22][CH:21]=1.[OH-].[Na+]>ClCCl>[Cl:8][C:6]1[N:7]=[C:2]([O:19][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[CH2:25])=[CH:22][CH:21]=2)[N:3]=[C:4]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])[N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 624534-VinylphenolHCID 110980692,4-dichloro-6-(2,4,6-trimethylphenoxy)-1,3,5-triazine

Product 1

HCID 23614955HCID 23614955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 25.57 g (0.09 moles) 2,4-dichloro-6-(2,4,6-trimethylphenoxy)-1,3,5-triazine in 300 ml of dichloromethane was treated with 11.8 g (0.098 moles) p-hydroxystyrene (prepared by hydrolysis of p-acetoxystyrene) dissolved in about 40 ml dichloromethane. The mixture was cooled in an ice-water bath and 36.8 g of 10% aqueous sodium hydroxide solution was added with stirring over about 5 minutes. Stirring was continued for 30 minutes after which time the ice-water bath was removed and stirring was continued for about 2 hours. The mixture was treated with brine, the layers were separated, and after standing, the organic layer was washed twice with brine, and once with water, and dried over magnesium sulfate. Filtration and evaporation gave a white solid with proton NMR spectrum consistent with the desired product, 2-chloro-4-(4-ethenylphenoxy)-6-(2,4,6-trimethylphenoxy)-1,3,5-triazine.

Workup

  1. temperatureThe mixture was cooled in an ice-water bath
  2. stirringStirring
  3. waitwas continued for 30 minutes
  4. customafter which time the ice-water bath was removed
  5. stirringstirring
  6. waitwas continued for about 2 hours
  7. additionThe mixture was treated with brine
  8. customthe layers were separated
  9. washthe organic layer was washed twice with brine
  10. dry with materialonce with water, and dried over magnesium sulfate
  11. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-09ed6479c6134e6b984b16a70719f50b
Source dataset
uspto-grants-2009_06
Patent number
US07547749B2

Reaction notes

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