Hydrochloric Acid → HCID 13013693, compound

HRID 868398Notes

Reaction equation

HRID 868398 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1Br.[OH:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([OH:22])=[O:21].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.C1(C)C=CC=CC=1.CCOCC.O>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[O:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:19]([CH:18]=1)[C:20]([OH:22])=[O:21]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 74203-Hydroxybenzoic AcidHCID 11430Potassium CarbonateHCID 1361642,4-Bis(trifluoromethyl)bromobenzene

Product 1

HCID 13013693HCID 13013693, compoundYield 7.1%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

2,4-Bis-trifluoromethylbromobenzene (5.86 g prepared by treatment of 2,4-di-carboxybromobenzene with hydrogen fluoride and sulphur tetrafluoride), 3-hydroxybenzoic acid (2.76 g) and anhydrous potassium carbonate (5.52 g) were heated in dimethylsulphoxide (5 ml) to 125°-130° for 14 hours. The mixture was cooled and poured into ice and water (500 ml). The mixture was acidified (HCl) and extracted with ether (300 ml). The extract was washed with water (2×300 ml), dried (MgSO4), and evaporated to give a solid. Further solid was obtained by re-extraction of the aqueous fractions with ether (250 ml). The solids were combined, taken up in hot toluene (60 ml) and diluted with petroleum (b.p. 60°-80°) to precipitate 3-hydroxybenzoic acid. The mixture was filtered and the filtrate evaporated to give a solid. This was washed with petroleum (b.p. 30°-40°). The washings were evaporated to give more solid. The solids were combined and re-crystallised from petroleum (b.p. 80°-100°) to give the required carboxylic acid (0.5 g) having a melting point of 133°-134°.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ether (300 ml)
  3. washThe extract was washed with water (2×300 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a solid
  7. customto precipitate 3-hydroxybenzoic acid
  8. filtrationThe mixture was filtered
  9. customthe filtrate evaporated
  10. customto give a solid
  11. washThis was washed with petroleum (b.p. 30°-40°)
  12. customThe washings were evaporated
  13. customto give more solid
  14. customre-crystallised from petroleum (b.p. 80°-100°)

Sources & evidence

ORD record
ord-2b1f7c7b0b764baab8d5eb7b49357423
Source dataset
uspto-grants-1988_10
Patent number
US04778914

Reaction notes

Loading…