Phenol → 2-chloro-4,6-diphenoxy-1,3,5-triazine

HRID 1390100Notes

Reaction equation

HRID 1390100 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-:17].[Na+]>CC(C)=O.O>[O:16]([C:2]1[N:4]=[C:5]([O:17][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[C:8]([Cl:9])[N:1]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 180882-chloro-4,6-diphenoxy-1,3,5-triazineYield 82.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 18.4 g (0.1 mole) of cyanuric chloride in 90 ml of acetone was added dropwise a solution of 19.0 g (0.2 moles) of phenol and 8.0 g (0.2 moles) of sodium hydroxide in 75 ml of water at a reaction temperature in the range of 15° to 20° C. After 41/2 hours the precipitate formed was removed by suction, washed with water and dried (with Mg SO4). Purification by recrystallization from n-heptane gave 24.7 g of 2,4-diphenoxy-6-chloro-s-triazine in 82% yield. The melting point was 119°-121° C.

Workup

  1. customAfter 41/2 hours the precipitate formed
  2. customwas removed by suction
  3. washwashed with water
  4. dry with materialdried (with Mg SO4)
  5. customPurification
  6. customby recrystallization from n-heptane

Sources & evidence

ORD record
ord-1395c42c2e4d4a1a976bf98bbb3eeedc
Source dataset
uspto-grants-1981_01
Patent number
US04247692

Reaction notes

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