M-Cresol → HCID 20298956, compound

HRID 1733406Notes

Reaction equation

HRID 1733406 reaction equation
[Na].Cl[C:3]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[CH:13]1[C:18]([OH:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20]>CO.[Cu]>[Cl:12][C:9]1[CH:8]=[C:4]([C:3]([O:19][C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:20])[CH:13]=2)=[CH:11][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 342M-CresolHCID 57842,5-Dichlorobenzoic acidHCID 5360545Sodium

Product 1

HCID 20298956HCID 20298956, compoundYield 32.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

Sodium (2.41 g) was dissolved in methanol and the solution placed under dry oxygen-free nitrogen. 2,5-Dichlorobenzoic acid (10 g), m-cresol (30 g) and activated copper powder (0.5 g) were added and the methanol removed by distillation. The temperature was increased to 180° with vigorous stirring and this temperature was maintained for 3 hours. The solution was cooled and steam distilled to remove the excess phenol. The resulting solution was filtered, cooled to room temperature and acidified with hydrochloric acid to give an oil. The oil slowly solidified; it was filtered off, dried, and washed with petroleum ether (30°-40° ). It was recrystallised at -10° from diethyl ether/petroleum ether (30°-40° ) to give, as a grey solid, the title compound (4.5 g), mp 124°-125° C.

Workup

  1. customthe methanol removed by distillation
  2. temperatureThe temperature was increased to 180°
  3. temperaturethis temperature was maintained for 3 hours
  4. temperatureThe solution was cooled
  5. distillationsteam distilled
  6. customto remove the excess phenol
  7. filtrationThe resulting solution was filtered
  8. customto give an oil
  9. filtrationit was filtered off
  10. customdried
  11. washwashed with petroleum ether (30°-40° )
  12. customIt was recrystallised at -10° from diethyl ether/petroleum ether (30°-40° )
  13. customto give, as a grey solid

Sources & evidence

ORD record
ord-908484919be94ff281fc9280a5831cd8
Source dataset
uspto-grants-1980_12
Patent number
US04242121

Reaction notes

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