Hydrochloric Acid → p-(Trifluoromethoxy)benzaldehyde

HRID 1650792Notes

Reaction equation

HRID 1650792 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.C([Li])CCC.CN(C)[CH:20]=[O:21].Cl>C(OCC)C.CCCCCC>[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:20]=[O:21])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 27772941-Iodo-4-(trifluoromethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 69573p-(Trifluoromethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 4-trifluoromethoxyiodobenzene (39.28 g.) in anhydrous diethyl ether (200 ml.) was added dropwise at -70° C. to n-butyl-lithium (96 ml. of a 1.6M solution in hexane) over 25 minutes. The solution was stirred for 30 minutes, and then dimethylformamide (14.83 g.) and anhydrous ether (50 ml.) were added over 15 minutes. After 1 hour, the solution was allowed to warm to -20° and was then hydrolysed by the addition of 3N hydrochloric acid (150 ml.). The organic layer was separated, and the aqueous layer was extracted twice with diethyl ether. The ether extracts were combined, washed with water, dried over magnesium sulphate and filtered, and the solvent was evaporated to give a yellow oil. Distillation of this oil gave 4-trifluoromethoxy benzaldehyde, b.p. 75°-7°/8 mm. of mercury, pressure.

Workup

  1. waitAfter 1 hour
  2. temperatureto warm to -20°
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customto give a yellow oil
  10. distillationDistillation of this oil

Sources & evidence

ORD record
ord-2bfd5ea37561448aa00e3b7b85129611
Source dataset
uspto-grants-1990_05
Patent number
US04925863

Reaction notes

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