Hydrochloric Acid → HCID 22009524, compound

HRID 376258Notes

Reaction equation

HRID 376258 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-].[Cs+].Cl.[CH2:22](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])[CH3:22])=[CH:17]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 25953Cesium fluorideHCID 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 heated to reflux with 7.2 g of cesium fluoride with nitrogen aeration for 12 h in 30 ml of N,N-diethylaniline. The mixture is stirred into 300 ml of 4 N hydrochloric acid after cooling, the resulting emulsion is extracted three times with 50 ml of ethyl acetate, and the organic extracts are combined, dried over ignited potassium carbonate and evaporated in vacuo. The residue is chromatographed on silica gel using toluene. After the evaporation of 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 the evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-0a008555ac9844b791e6048c5d813692
Source dataset
uspto-grants-2000_02
Patent number
US06020340

Reaction notes

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