Hydrochloric Acid → p-(Trifluoromethoxy)benzaldehyde

HRID 1441049Notes

Reaction equation

HRID 1441049 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[F:11][C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#N)=[CH:18][CH:17]=1)([F:14])[F:13].[O:24]1CCOCC1.Cl>C(OCC)C.O>[F:11][C:12]([F:14])([F:13])[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[O:24])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 676214-(Trifluoromethoxy)benzonitrileHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 69573p-(Trifluoromethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Diisobutylaluminium hydride (11.8 ml. 1M solution in toluene) was added to a stirred solution of 4-cyanophenyl trifluoromethyl ether (2.0 g., Fairfield) in dry diethyl ether (100 ml.). The mixture was refluxed with stirring for 3 hours. The mixture was cooled and dioxane (5 ml.) containing water 1.0 ml.) was added. Dilute hydrochloric acid was added (60 ml. of 10% solution). The mixture was stirred for 30 minutes and extracted with diethyl ether. The ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and the residue was purified by chromatography on silica, eluting with 9:1 hexane:diethyl ether. 4-Trifluoromethoxybenzaldehyde was obtained as a colourless liquid (1.65 g.).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureThe mixture was cooled
  3. addition) was added
  4. stirringThe mixture was stirred for 30 minutes
  5. extractionextracted with diethyl ether
  6. washThe ethereal extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by chromatography on silica
  10. washeluting with 9:1 hexane

Sources & evidence

ORD record
ord-7c173880cb27470680db651cd27692ae
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

Loading…