Hydrochloric Acid → 5-tert-Butyl-2-hydroxy-3-(trifluoromethyl)benzaldehyde

HRID 1576004Notes

Reaction equation

HRID 1576004 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[OH:13].O.Cl.FC(F)(F)[C:20](O)=[O:21]>>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:8]=[C:7]([C:9]([CH3:11])([CH3:12])[CH3:10])[CH:6]=[C:5]([CH:20]=[O:21])[C:4]=1[OH:13]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6422Trifluoroacetic acidHCID 126521024-tert-Butyl-2-(trifluoromethyl)phenol

Product 1

HCID 198618175-tert-Butyl-2-hydroxy-3-(trifluoromethyl)benzaldehyde

Procedure

0.1 mole of 2-trifluoromethyl-4-tert-butylphenol and 0.1 mole of hexamethylenetretramine is dissolved in trifluoroacetic acid (150 ml.) and the mixture refluxed for 8 hours. After this time, 150 ml. of water and 50 ml. of concentrated hydrochloric acid is added. This mixture is then refluxed for 1/2 hour. The reaction mixture is cooled and extracted with ether (5 × 50 ml.) and the ether extract is dried over magnesium sulfate. The ether is evaporated and the residue is crystallized from ethanol to yield 3-trifluoromethyl-5-t-butyl salicylaldehyde.

Workup

  1. temperaturethe mixture refluxed for 8 hours
  2. temperatureThis mixture is then refluxed for 1/2 hour
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with ether (5 × 50 ml.)
  5. extractionthe ether extract
  6. dry with materialis dried over magnesium sulfate
  7. customThe ether is evaporated
  8. customthe residue is crystallized from ethanol

Sources & evidence

ORD record
ord-fd11b908173946d0a7312fc2317cfc5e
Source dataset
uspto-grants-1976_09
Patent number
US03979361

Reaction notes

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