3-Hydroxybenzoic Acid → HCID 18801618, compound

HRID 435411Notes

Reaction equation

HRID 435411 reaction equation
[OH-].[K+].[OH:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1>CO.CS(C)=O.O.C1(C)C=CC=CC=1>[C:7]([C:6]1[CH:5]=[C:4]([CH:12]=[CH:11][CH:10]=1)[O:3][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][N:21]=1)([OH:9])=[O:8]

Participants

9

Reactant 4

HCID 74203-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 18801618HCID 18801618, compoundYield 84.8%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of potassium hydroxide (1.32 g; 85% pellets) in dry methanol (25 ml) was treated at room temperature with metahydroxybenzoic acid (1.38 g) to give a solution. This was stirred for 30 minutes and then coevaporated with added toluene to give a white solid. The solid was dispersed in dry dimethylsulphoxide (10 ml.) Anhydrous potassium carbonate (0.5 g) and 2-chloro-5-trifluoromethylpyridine (1.82 g) were added, and the solution stirred. After 64 hours, water (100 ml) was added. The mixture was extracted with chloroform, filtered and brought to pH 1 with concentrated hydrochloric acid. The solid which precipitated was washed with water and dried to give 2-(3-carboxyphenoxy)-5-trifluoromethylpyridine (2.4 g) (m.p. 146° C.).

Workup

  1. customto give a solution
  2. customto give a white solid
  3. additionwere added
  4. stirringthe solution stirred
  5. waitAfter 64 hours
  6. extractionThe mixture was extracted with chloroform
  7. filtrationfiltered
  8. customThe solid which precipitated
  9. washwas washed with water
  10. customdried

Sources & evidence

ORD record
ord-d6783091c25043809968baa93faa4e38
Source dataset
uspto-grants-1983_08
Patent number
US04401460

Reaction notes

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