Hydrochloric Acid → 3-Methyl-4-(trifluoromethyl)benzoic acid

HRID 900848Notes

Reaction equation

HRID 900848 reaction equation
[CH3:1][C:2]1[CH:3]=C([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])C#N.[OH-:14].[Na+].Cl.[O:17]1[CH2:22][CH2:21]OCC1>CC(OC)(C)C>[CH3:1][C:2]1[CH:3]=[C:21]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[C:22]([OH:17])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 574686963-Methyl-4-(trifluoromethyl)benzonitrile

Product 1

HCID 666504483-Methyl-4-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 3-methyl-4-trifluoromethyl-benzonitrile from step 5 (16.25 g, 88 mmol) and 3 N NaOH (88 mL, 264 mmol) in dioxane (90 mL) was refluxed for 18 h. The mixture was cooled to 23° C., diluted with TBME, acidified with 1 N HCl to pH 1 and extracted twice with TBME. The combined organic layers were washed with brine, dried over MgSO4. Removal of the solvent in vacuum left the title compound as an off white solid (14.46 g, 81%), %), which was used without further purification. MS (ISN) 203.1 [M−H].

Workup

  1. temperaturewas refluxed for 18 h
  2. extractionextracted twice with TBME
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent in vacuum
  6. waitleft the title compound as an off white solid (14.46 g, 81%)
  7. custom%), which was used without further purification

Sources & evidence

ORD record
ord-c945f1a2ee004ab4b8143d97ceddfe48
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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