P-Cresol → Benzene, 1,1'-oxybis[4-methyl-

HRID 2398778Notes

Reaction equation

HRID 2398778 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH:9]1[C:14]([OH:15])=[CH:13][CH:12]=[C:11]([CH3:16])[CH:10]=1.[OH-].[K+]>[Cu]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([O:15][C:14]2[CH:9]=[CH:10][C:11]([CH3:16])=[CH:12][CH:13]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 78054-BromotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 74098Benzene, 1,1'-oxybis[4-methyl-

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
190 °C

Procedure

p-Bromotoluene (51g), p-cresol (33g) and potassium hydroxide (18.5 g) were mechanically stirred on a steam bath for 30 min., then heated at 190° C. for 1 hr. Copper bronze (2.0g) was added and the heating continued for a further 1 hr. at 190° C., then 220° to 230° C. for 2.5 hr. After cooling, the residue was extracted into chloroform, filtered, and the extract washed with water, dried, evaporated and crystallised from ethanol to yield 4,4'-dimethyldiphenyl ether, m.p. 49°-50° C.

Workup

  1. waitat 190° C., then 220° to 230° C. for 2.5 hr
  2. temperatureAfter cooling
  3. extractionthe residue was extracted into chloroform
  4. filtrationfiltered
  5. washthe extract washed with water
  6. customdried
  7. customevaporated
  8. customcrystallised from ethanol

Sources & evidence

ORD record
ord-ab21a19d330b46f1b1f26a65b4b180fd
Source dataset
uspto-grants-1977_05
Patent number
US04025635

Reaction notes

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