Acetic Acid → 4-(4'-Fluoro-2'-methoxyphenyl)-phenol

HRID 442271Notes

Reaction equation

HRID 442271 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:14]=[CH:13][C:11](N)=[CH:10][CH:9]=2)=[C:4]([O:15][CH3:16])[CH:3]=1.C(O)(=[O:19])C.N([O-])=O.[Na+].S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:14]=[CH:13][C:11]([OH:19])=[CH:10][CH:9]=2)=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 214164544'-Fluoro-2'-methoxy[1,1'-biphenyl]-4-amineHCID 23668193Sodium Nitrite

Product 1

HCID 214164764-(4'-Fluoro-2'-methoxyphenyl)-phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 32.00 grams of 4-(4'-fluoro-2'-methoxyphenyl)-aniline in 120 ml. of glacial acetic acid is cooled to 10° - 12° C. To this solution is added slowly a solution of 12.25 grams of sodium nitrite in 120 ml. of water with stirring and continued cooling. Five minutes after this addition, the suspension of the diazonium acetate is added slowly to a boiling solution of 100 ml. of concentrated sulfuric acid and 200 ml. of water. After the final addition of the diazonium salt, the suspension is boiled for an additional 5 minutes and then allowed to cool to room temperature. The reaction mixture is then filtered and the cake dried in vacuo to yield 4-(4'-fluoro-2'-methoxyphenyl)-phenol.

Workup

  1. temperaturecontinued cooling
  2. additionFive minutes after this addition
  3. additionis added slowly to a boiling solution of 100 ml
  4. filtrationThe reaction mixture is then filtered
  5. customthe cake dried in vacuo

Sources & evidence

ORD record
ord-7a2e3c909d6346a2a62d892e5915bc0b
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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