3-Hydroxybenzoic Acid → HCID 881944, compound

HRID 868458Notes

Reaction equation

HRID 868458 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29]>CN(C)C=O>[N+:28]([C:19]1[CH:20]=[C:21]([C:24]([F:25])([F:26])[F:27])[CH:22]=[CH:23][C:18]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6])([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 74203-Hydroxybenzoic AcidHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium Carbonate

Product 1

HCID 881944HCID 881944, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxybenzoic acid (13.8 g) in dry dimethylformamide (100 ml) was heated and stirred for 7 hours at 100° with anhydrous potassium carbonate (26 g) and 4-chloro-3-nitrobenzotrifluoride (22.5 g). The mixture was then evaporated to a small volume under reduced pressure and diluted with water. With warming, a dark solution was obtained. Acidification gave a white precipitate; this was washed with water and recrystallised from a mixture of methanol and water to give 3(2-nitro-4-trifluoromethylphenoxy) benzoic acid (24 g).

Workup

  1. customThe mixture was then evaporated to a small volume under reduced pressure
  2. additiondiluted with water
  3. temperatureWith warming
  4. customa dark solution was obtained
  5. customAcidification gave a white precipitate
  6. washthis was washed with water
  7. customrecrystallised from a mixture of methanol and water

Sources & evidence

ORD record
ord-71885830fb554d7da73e2ee9707f46b1
Source dataset
uspto-grants-1988_10
Patent number
US04780128

Reaction notes

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