Phenol → 2-Methyl-4-nitro-1-phenoxybenzene

HRID 1781153Notes

Reaction equation

HRID 1781153 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[CH3:18]>>[CH3:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 186166912-Methyl-4-nitro-1-phenoxybenzene

Conditions

Temperature
60 °C

Procedure

Using phenol and 2-fluoro-5-nitrotoluene and the procedures described in Example 52A, except the reaction was heated to 60° C. overnight and vacuum distilled at 4.5 mm Hg, 174°-5° C., provided 3-methyl-4-phenoxynitrobenzene. 1H NMR (CDCl3) δ 8.16 (dd, 1H), 8.00 (dd, 1H), 7.42 (m, 2H), 7.23 (m, 1H), 7.05 (m, 2H), 6.78 (d, 1H),2.42 (s, 3H). MS (DCl/NH3) role 247 (M+H)+.

Workup

  1. distillationvacuum distilled at 4.5 mm Hg, 174°-5° C.

Sources & evidence

ORD record
ord-3544623d1de2487d8d6e88d0e1269194
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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