Pyridine → HCID 20348062, compound

HRID 1701081Notes

Reaction equation

HRID 1701081 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].C[C:11]([CH3:14])([O-])[CH3:12].[K+].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=C[CH:26]=[CH:25][CH:24]=1>>[O:4]([C:3]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][C:12]2[CH:11]=[CH:14][CH:26]=[CH:25][CH:24]=2)[C:2]=1[CH3:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 7961BromobenzeneHCID 118432-MethylresorcinolHCID 23665647Potassium tert-butoxide

Product 1

HCID 20348062HCID 20348062, compound

Procedure

A mixture of 4 parts of 2-methylresorcinol, 7 parts of potassium tert-butoxide, 11 parts of bromobenzene, 1 part cuprous chloride and 70 parts of pyridine is distilled until the temperature reaches 115°, and then is heated under reflux for 15 hours. The mixture is then added to 100 parts of ice water, made acidic with concentrated hydrochloric acid and extracted several times with toluene. The toluene extracts are dried over anhydrous potassium carbonate, concentrated and distilled to give 2,6-diphenoxytoluene, B.P. 146°-156° (0.2 torr), M.P. 39°-41°.

Workup

  1. distillationis distilled until the temperature
  2. customreaches 115°
  3. temperatureis heated
  4. temperatureunder reflux for 15 hours
  5. additionThe mixture is then added to 100 parts of ice water
  6. extractionextracted several times with toluene
  7. dry with materialThe toluene extracts are dried over anhydrous potassium carbonate
  8. concentrationconcentrated
  9. distillationdistilled

Sources & evidence

ORD record
ord-7206bc6505ce44bf80e2bf2c371a8265
Source dataset
uspto-grants-1980_03
Patent number
US04191554

Reaction notes

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