Ammonia → 1-Nitro-4-phenoxybenzene

HRID 1769827Notes

Reaction equation

HRID 1769827 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]1([O-:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Na+].N>>[CH:14]1[CH:15]=[CH:16][C:11]([O:17][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 74741-Chloro-4-nitrobenzeneHCID 4445035Phenolate Sodium

Product 1

HCID 121101-Nitro-4-phenoxybenzene

Conditions

Temperature
70 °C

Procedure

157.6 g of p-chloronitrobenzene and 116.1 g of sodium phenolate were initially introduced into a steel autoclave. At room temperature, 100 g of liquid ammonia were pumped into the pressure vessel, the mixture was heated to 70° C. and allowed to completely react with stirring over a period of 9 hours. The pressure of 28 bar initially observed dropped during the reaction to 22 bar. Removal of the ammonia by distillation and workup of the distillation residue gave-4-nitrodiphenyl ether with a yield of 213.8 g=99.4% of the theoretical yield. The product is 99.2% pure.

Workup

  1. customAt room temperature
  2. customto completely react
  3. additionThe pressure of 28 bar initially observed dropped during the reaction to 22 bar
  4. customRemoval of the ammonia
  5. distillationby distillation and workup of the distillation residue

Sources & evidence

ORD record
ord-acbb5e5af817455c8b67aa5dd55217d5
Source dataset
uspto-grants-1995_01
Patent number
US05382686

Reaction notes

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