Acetic Acid → Benzonitrile, 2-(4-(methylsulfonyl)phenoxy)-5-nitro-

HRID 1155738Notes

Reaction equation

HRID 1155738 reaction equation
[CH3:1][S:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:9]=2[C:10]#[N:11])=[CH:5][CH:4]=1.OO.[OH2:23].C(O)(=[O:26])C>>[CH3:1][S:2]([C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:9]=2[C:10]#[N:11])=[CH:5][CH:4]=1)(=[O:26])=[O:23]

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 784Hydrogen PeroxideHCID 962WaterHCID 514855Benzonitrile, 2-(4-(methylthio)phenoxy)-5-nitro-

Product 1

HCID 514856Benzonitrile, 2-(4-(methylsulfonyl)phenoxy)-5-nitro-Yield 98.2%

Conditions

Temperature
75 °C

Procedure

To a slurry of 10.0 g (0.0350 moles) of 2-(4-(methylthio)phenoxy)-5-nitrobenzonitrile in 75 ml of glacial acetic acid heated at 60° C. was added 15.85 g of aqueous 30% hydrogen peroxide (0.140 moles) over 5 minutes. An additional 25 ml of glacial acetic acid was added and the mixture heated at 75° C. for 3 hrs. The reaction mixture was cooled and poured into water. The product was collected by filtration, washed with water and dried to obtain 10.9 g of product (98.2% yield), mp 205°-206.5° C. Recrystallization from methanol gave purified 2-(4-(methylsulfonyl)phenoxy)-5-nitrobenzonitrile, mp 206°-207° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-834a6410ab954c60bce2686fbcc7f5d1
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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