Hydrochloric Acid → HCID 22009524, compound

HRID 322035Notes

Reaction equation

HRID 322035 reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][C:5]=1[O:12][C:13]([CH3:17])([C:15]#[CH:16])C.[F-].Cl.[CH2:21](N(CC)C1C=CC=CC=1)C>>[F:18][CH:2]([F:1])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]2[C:5]=1[O:12][C:13]([CH:15]([CH3:16])[CH3:21])=[CH:17]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 28179Fluoride IonHCID 22009532HCID 22009532, compound

Product 1

HCID 22009524HCID 22009524, compound

Procedure

5.5 g of 4-difluoromethoxy-3-(2-methyl-3-butyn-2-yloxy)benzaldehyde are refluxed with 7.2 g of cesitum fluoride for 12 h with nitrogen aeration in 30 ml of N,N-diethylaniline. After cooling, the mixture is stirred into 300 ml of 4 N hydrochloric acid, the resulting emulsion is extracted three times with 50 ml of ethyl acetate, and the organic extracts are combined, dried over calcined potassium carbonate and evaporated in vacuo. The residue is chromatographed on silica gel using toluene. After evaporating the appropriate fractions, the title compound is obtained as an oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting emulsion is extracted three times with 50 ml of ethyl acetate
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue is chromatographed on silica gel
  6. customAfter evaporating the appropriate fractions

Sources & evidence

ORD record
ord-60c05fbe87e24a368f161baabf0284c6
Source dataset
uspto-grants-2001_04
Patent number
US06211203B1

Reaction notes

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