Hydrochloric Acid → 2-Hydroxy-3-(trifluoromethyl)benzaldehyde

HRID 385011Notes

Reaction equation

HRID 385011 reaction equation
COC[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([F:14])([F:13])[F:12].C([Li])CCC.CCCCCC.CN(C)[CH:28]=[O:29].Cl>O1CCCC1>[OH:4][C:5]1[C:6]([C:11]([F:12])([F:13])[F:14])=[CH:7][CH:8]=[CH:9][C:10]=1[CH:28]=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 109436391-Methoxymethoxy-2-(trifluoromethyl)benzeneHCID 178418244HCID 178418244, compound

Product 1

HCID 27792742-Hydroxy-3-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-methoxymethoxy-2-trifluoromethylbenzene (64.13 g) was dissolved in tetrahydrofuran (500 mL), and a 2.77M n-butyllithium-n-hexane solution (123 mL) was added to the solution over 45 minutes under an argon gas flow at −70° C., and then the mixture was stirred for 1 hour. N,N-dimethylformamide (28.5 mL) was added, followed by stirring at room temperature for 30 minutes. 4N hydrochloric acid (310 mL) was added, followed by stirring at 60° C. for 19 hours. The organic solvent was distilled off under reduced pressure, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (59.16 g) as a yellow crystal.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. stirringby stirring at 60° C. for 19 hours
  3. distillationThe organic solvent was distilled off under reduced pressure
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-71378d63320342248b41093ad8d78210
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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