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Sodium Hydroxide → [1,1'-Biphenyl]-2-carboxylic acid, 6-methyl-4'-(trifluoromethyl)-

HRID 1531311
Notes
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Reaction equation

HRID 1531311 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:20]([O:22]C)=[O:21])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1>CO.O>[CH3:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([C:20]([OH:22])=[O:21])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:12][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11833278Methyl 6-methyl-4'-trifluoromethylbiphenyl-2-carboxylate

Product 1

HCID 10945826[1,1'-Biphenyl]-2-carboxylic acid, 6-methyl-4'-(trifluoromethyl)-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6N Sodium hydroxide (260 mL) is added slowly at room temperature to a solution of 183 g of methyl 6-methyl-4′-trifluoromethyl-biphenyl-2-carboxylate in 1200 mL of methanol. The reaction mixture is heated under gentle reflux for 2.5 hours, cooled to room temperature and diluted with 300 mL of water. The reaction mixture is evaporated under reduced pressure (110-120 mbar/40° C.) to a suspension of about 750 mL which is filtered through the filter agent Celite® 521, and the filter cake is washed sequentially with 250 mL of water and 250 mL of heptane. The organic layer is separated and the aqueous layer is washed with 250 mL of heptane. The aqueous layer is acidified with 500 mL of 4N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract is washed with water and filtered through the filter agent Celite® 521. The ethyl acetate solution (ca. 1000 mL) is evaporated under reduced pressure (110-120 mbar/40° C.) to a volume of 600 mL to which is added heptane (3125 mL). The suspension is then heated to reflux until a clear solution is obtained, the solution is cooled to 0° C. and the resulting solid is filtered off to yield 6-methyl-4′-trifluoromethyl-biphenyl-2-carboxylic acid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder gentle reflux for 2.5 hours
  3. customThe reaction mixture is evaporated under reduced pressure (110-120 mbar/40° C.) to a suspension of about 750 mL which
  4. filtrationis filtered through the filter agent Celite® 521
  5. washthe filter cake is washed sequentially with 250 mL of water and 250 mL of heptane
  6. customThe organic layer is separated
  7. washthe aqueous layer is washed with 250 mL of heptane
  8. extractionextracted with ethyl acetate
  9. extractionThe ethyl acetate extract
  10. washis washed with water
  11. filtrationfiltered through the filter agent Celite® 521
  12. customThe ethyl acetate solution (ca. 1000 mL) is evaporated under reduced pressure (110-120 mbar/40° C.) to a volume of 600 mL to which
  13. additionis added heptane (3125 mL)
  14. temperatureThe suspension is then heated
  15. temperatureto reflux until a clear solution
  16. customis obtained
  17. temperaturethe solution is cooled to 0° C.
  18. filtrationthe resulting solid is filtered off

Sources & evidence

ORD record
ord-aa00a68ed7734957b3f7ff0fbe6c6742
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06197798B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes