2,5-Dichlorobenzoic acid → HCID 20298962, compound

HRID 1733404Notes

Reaction equation

HRID 1733404 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1.[H-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:11][C:8]1[CH:7]=[C:3]([C:2]([O:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:13]([F:12])([F:21])[F:22])[CH:15]=2)=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydride

Product 1

HCID 20298962HCID 20298962, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2,5-Dichlorobenzoic acid (5 g) and 3-trifluoromethylphenol (4.24 g) were dissolved in xylene and the solution placed under dry oxygen-free nitrogen. Sodium hydride (1.25 g) was slowly added and when effervescence had ceased, cuprous bromide was added and the solution or suspension refluxed for 6 hours. The xylene was removed by low pressure distillation. The solid residue was treated with water and acidified with dilute hydrochloric acid. The resulting oil was extracted into diethyl ether and the ether removed by low pressure distillation to give a light yellow solid which was recrystallised from diethyl ether/petroleum ether to give the title compound (2.7 g), mp, 124° C.

Workup

  1. temperaturethe solution or suspension refluxed for 6 hours
  2. customThe xylene was removed by low pressure distillation
  3. additionThe solid residue was treated with water
  4. extractionThe resulting oil was extracted into diethyl ether
  5. customthe ether removed by low pressure distillation
  6. customto give a light yellow solid which
  7. customwas recrystallised from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-01cf0b4a2867480f905e3a18fe4c50c4
Source dataset
uspto-grants-1980_12
Patent number
US04242121

Reaction notes

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