Acetic Acid → 2-Fluoro-5-methyl-4-nitrophenol

HRID 371682Notes

Reaction equation

HRID 371682 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[C:9](O)(=O)C.S(=O)(=O)(O)O.[N:18]([O-:20])=[O:19].[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([N+:18]([O-:20])=[O:19])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 97072-FluorophenolHCID 23668193Sodium Nitrite

Product 1

HCID 224146402-Fluoro-5-methyl-4-nitrophenolYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 26.6 grams (0.21 mole) of the fluorophenol in 63 ml. of acetic acid and 8.5 ml. of sulfuric acid was stirred at 8°-12° C. While the mixtute was cooled and stirred, a solution of 15 grams of sodium nitrite in 42 ml. of water was added dropwise over a period of about 1 hour. Stirring was continued for an additional 30 minutes. The mixture then was poured into a large volume of ice water. The resulting crude product was collected by filtration, thoroughly washed with water, and air dried while on the filter. The resulting crude nitroso compound then was added in portions to a stirred solution of 20 ml. of 70 percent nitric acid and 60 ml. of water maintained at 40°-50° C. Heating and stirring were continued until the evolution of brown fumes became negligible. The mixture then was poured into ice water, and the crude product was collected. The crude product then was recrystallized from ethanol-water to obtain a first and a second crop. A total of 25.4 grams (70 percent) of 2-fluoro-4-nitro-5-methylphenol was obtained, m.p. 110°-111.5° C.

Workup

  1. temperatureWhile the mixtute was cooled
  2. stirringStirring
  3. filtrationThe resulting crude product was collected by filtration
  4. washthoroughly washed with water, and air
  5. customdried while on the filter
  6. additionThe resulting crude nitroso compound then was added in portions to a stirred solution of 20 ml
  7. temperatureof water maintained at 40°-50° C
  8. temperatureHeating
  9. stirringstirring
  10. additionThe mixture then was poured into ice water
  11. customthe crude product was collected
  12. customThe crude product then was recrystallized from ethanol-water
  13. customto obtain a first and a second crop

Sources & evidence

ORD record
ord-e8d5d1e8337042258f156cb7d499ab38
Source dataset
uspto-grants-1978_05
Patent number
US04087444

Reaction notes

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