Sodium Hydroxide → 2-Chloro-5-(trifluoromethyl)benzoic acid

HRID 974205Notes

Reaction equation

HRID 974205 reaction equation
[Cl:1][C:2]1C=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1C#N.[OH-].[Na+].[C:16]([O:19]CC)(=[O:18])[CH3:17].CCCCCC>O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:17]=1[C:16]([OH:19])=[O:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 676042-Chloro-5-(trifluoromethyl)benzonitrileHCID 21226206Ethyl acetate hexane

Product 1

HCID 6881822-Chloro-5-(trifluoromethyl)benzoic acidYield 9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 962WaterSolvent

Procedure

A solution of 570 g (2.77 moles) of 2-chloro-5-trifluoromethylbenzonitrile (1) and 1140 g (28.5 moles) NaOH in 2.3 L water was heated at reflux in a 12 L flask overnight. TLC (silica gel, 20% ethyl acetate-hexane with 1 drop acetic acid/10 ml solution) showed reaction was complete. The solution was cooled, diluted with 3.5 L ice water and extracted with 1 liter ether. The aqueous extract was cooled in an ice bath, acidified to pH 2 with cold 50% H2SO4 and extracted with four 1.3 liter portions of ether. The ether extracts were dried over Na2SO4 and evaporated and the residue was triturated with 1.2 liters hot hexane, cooled, and filtered to afford 615 g (9%) of 2-chloro-5-trifluoromethylbenzoic acid as white needles, m.p. 93°-94° C.

Workup

  1. temperatureat reflux in a 12 L flask overnight
  2. customreaction
  3. temperatureThe solution was cooled
  4. extractionextracted with 1 liter ether
  5. extractionThe aqueous extract
  6. temperaturewas cooled in an ice bath
  7. extractionextracted with four 1.3 liter portions of ether
  8. dry with materialThe ether extracts were dried over Na2SO4
  9. customevaporated
  10. customthe residue was triturated with 1.2 liters hot hexane
  11. temperaturecooled
  12. filtrationfiltered

Sources & evidence

ORD record
ord-3feccc556c764f148cd5346ba3f4717d
Source dataset
uspto-grants-1991_11
Patent number
US05068248

Reaction notes

Loading…