P-Cresol → 1-Methyl-4-(4-nitrophenoxy)benzene

HRID 1065279Notes

Reaction equation

HRID 1065279 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.CC(C)([O-])C.[K+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1>C(O)(C)(C)C>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:7][C:6]2[CH:5]=[CH:4][C:3]([CH3:8])=[CH:2][CH:1]=2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 2879P-CresolHCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 769431-Methyl-4-(4-nitrophenoxy)benzene

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

p-Cresol (190 g; 1.76 mol), potassium-tert-butoxide (220.2 g; 1.93 mol) and t-butanol (from calcium hydride; 1 l) were stirred at room temperature, under nitrogen, for 15 mins; followed by the dropwise addition of p-fluoronitrobenzene (272.7 g; 1.93 mol). After heating at reflux for 18 hours, followed by cooling, the resulting yellow precipitate was removed by filtration and washed with absolute ethanol. The combined filtrate and washings were evaporated on the Buchi and the residue taken up in benzene (4 l). The combined benzene layers were dried over magnesium sulphate and evaporated to yield a yellow residue which was recrystallised from hexane (2 l) to give 4-(4-nitrophenoxy)toluene as a yellow solid. m.p. 65°-66° C. NMR (CDCl3): 8.01 (d, 2H), 7.5 (q, 6H) and 2.31 (s, 3H). Analysis for C13H11NO3 : Calculated: C, 68.10, H, 4.84, N, 6.11; found: C, 68.13; H, 4.87; N, 6.14.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 18 hours
  3. temperatureby cooling
  4. customthe resulting yellow precipitate was removed by filtration
  5. washwashed with absolute ethanol
  6. customThe combined filtrate and washings were evaporated on the Buchi
  7. dry with materialThe combined benzene layers were dried over magnesium sulphate
  8. customevaporated
  9. customto yield a yellow residue which
  10. customwas recrystallised from hexane (2 l)

Sources & evidence

ORD record
ord-e63dc4a1fe724f3b86cf255aa3d9381f
Source dataset
uspto-grants-1982_05
Patent number
US04329365

Reaction notes

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