Guaiacol → 5-Chloro-2-(2'-methoxyphenoxy)benzoic acid

HRID 1414571Notes

Reaction equation

HRID 1414571 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].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].C[O-].[Na+].[Na]>CO.[Cu]>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([O:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH3:12])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 460GuaiacolHCID 57842,5-Dichlorobenzoic acidHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 234605225-Chloro-2-(2'-methoxyphenoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of 2,5-dichlorobenzoic acid (9.5 g.), 2-methoxyphenol (7.4 g.) and copper bronze (1.0 g.) is added to a solution of sodium methoxide in methanol prepared from sodium (2.53 g.) and methanol (50 ml.). The excess methanol is evaporated and 1,2-dichlorobenzene (50 ml.) is added to the residue. The mixture is stirred and heated under reflux for 2.5 hours. The mixture is cooled, acidified with 3N hydrochloric acid, filtered to remove copper bronze and extracted with chloroform. The organic layer is separated and extracted with saturated sodium hydrogen carbonate solution. The sodium hydrogen carbonate extract is acidified. The precipitate is filtered off, dissolved in toluene, and the toluene solution treated with carbon, filtered and the solvent evaporated. The solid residue is recrystallised from toluene-petroleum ether (b.p. 60°-80° C.) to give 5-chloro-2-(2'-methoxyphenoxy)benzoic acid, m.p. 115°-118° C.

Workup

  1. customThe excess methanol is evaporated
  2. addition1,2-dichlorobenzene (50 ml.) is added to the residue
  3. temperatureheated
  4. temperatureunder reflux for 2.5 hours
  5. temperatureThe mixture is cooled
  6. filtrationfiltered
  7. customto remove copper bronze
  8. extractionextracted with chloroform
  9. customThe organic layer is separated
  10. extractionextracted with saturated sodium hydrogen carbonate solution
  11. extractionThe sodium hydrogen carbonate extract
  12. filtrationThe precipitate is filtered off
  13. dissolutiondissolved in toluene
  14. additionthe toluene solution treated with carbon
  15. filtrationfiltered
  16. customthe solvent evaporated
  17. customThe solid residue is recrystallised from toluene-petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-a5c8a006789446f0b0b26cf189c3d0d1
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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