Acetic Acid → HCID 21320318, compound

HRID 262226Notes

Reaction equation

HRID 262226 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([N+:12]([O-:14])=[O:13])=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1.C(O)(=[O:24])C.OO.[OH2:28]>>[CH3:1][S:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([N+:12]([O-:14])=[O:13])=[C:9]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:8]=2[CH:21]=1)(=[O:24])=[O:28]

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 784Hydrogen PeroxideHCID 962WaterHCID 21320301HCID 21320301, compound

Product 1

HCID 21320318HCID 21320318, compound

Conditions

Temperature
20 °C

Procedure

A mixture of 2.8 g. (0.009 mole) of 5-methylthiomethyl-2-nitro-3-phenylbenzofuran and 160 ml. of acetic acid is heated to 40° C., and 2.0 g. (0.018 mole) of hydrogen peroxide in 30 ml. of acetic acid is added dropwise as the temperature rises to 50° C. The solution is stirred for about six hours at 50° C. and for about 16 hours at 20° C., then poured into cold water. The precipitate is collected by filtration, rinsed with water and dissolved in dichloromethane. The solution is washed with water and saturated sodium chloride solution, then dried. Evaporation provides yellow solid which is recrystallized from a benzene-hexane mixture to give 5-methylsulfonylmethyl-2-nitro-3-phenylbenzofuran, m.p. 178°-181° C.

Workup

  1. additionA mixture of 2.8 g
  2. customrises to 50° C
  3. filtrationThe precipitate is collected by filtration
  4. washrinsed with water
  5. dissolutiondissolved in dichloromethane
  6. washThe solution is washed with water and saturated sodium chloride solution
  7. customdried
  8. customEvaporation
  9. customprovides yellow solid which
  10. customis recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-bb0961efe26544cd9bc0c4ca2633e311
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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