Phenol → HCID 20514081, compound

HRID 1902885Notes

Reaction equation

HRID 1902885 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].Cl[C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[N:13]=1>>[CH3:18][C:16]1[CH:17]=[C:12]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:13]=[C:14]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[N:15]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 10942334Sodium MethoxideHCID 17606429HCID 17606429, compound

Product 1

HCID 20514081HCID 20514081, compoundYield 86.7%

Conditions

Temperature
160 °C

Procedure

A mixture of 250 g of phenol and 29.7 g of sodium methylate is heated to an interval temperature of 160° C. while simultaneously distilling off methanol. The melt obtained is cooled to 120° C., then 109 g of 4-chloro-6-methyl-2-p-tolylpyrimidine are added and the mixture is stirred for 3 hours at 120° C. After cooling, excess phenol is removed with steam, and the residue is filtered with suction, washed with water and dried. Recrystallisation from methanol yields 119.4 g (86.5% of theory) of 4-methyl-6-phenoxy-2-p-tolylpyrimidine with a melting point of 90°-91° C.

Workup

  1. distillationwhile simultaneously distilling off methanol
  2. customThe melt obtained
  3. temperatureis cooled to 120° C.
  4. temperatureAfter cooling
  5. customexcess phenol is removed with steam
  6. filtrationthe residue is filtered with suction
  7. washwashed with water
  8. customdried
  9. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-2ffd53ce13f94c52a5a4316a9ebfb2d6
Source dataset
uspto-grants-1982_12
Patent number
US04366189

Reaction notes

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