Hydrochloric Acid → HCID 21404983, compound

HRID 267874Notes

Reaction equation

HRID 267874 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=[CH:7][C:8]=1[O:9]C.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:17])([CH3:16])[CH3:18])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 795486N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2-dimethylpropanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21404983HCID 21404983, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Dissolve 0.53 g. of N-[β-(3,4-dimethoxyphenyl)-ethyl]-2,2-dimethylpropionamide in 10 ml. of benzene and 15 g. of aluminum chloride. Reflux the mixture overnight (17 hours) with vigorous stirring. Cool the mixture to room temperature and, cautiously, pour the reaction mixture into dilute hydrochloric acid and ice with vigorous stirring. Separate the liquid phases and discard the benzene layer. Extract the aqueous layer with ethyl-acetate, then wash the extract with saturated sodium bicarbonate and water. Dry the extract over anhydrous sodium sulfate, filter and vaporate to a residue. Crystallize the residue from a 9:1 mixture of toluene:ethanol to obtain the title product.

Workup

  1. dissolutionDissolve 0.53 g
  2. temperatureReflux the mixture overnight (17 hours) with vigorous stirring
  3. customSeparate the liquid phases
  4. extractionExtract the aqueous layer with ethyl-acetate
  5. washwash the
  6. extractionextract with saturated sodium bicarbonate and water
  7. customDry the
  8. extractionextract over anhydrous sodium sulfate
  9. filtrationfilter
  10. customCrystallize the residue
  11. additionfrom a 9:1 mixture of toluene

Sources & evidence

ORD record
ord-cc6deb2a93a141049e5fad5d0fbf013a
Source dataset
uspto-grants-1976_03
Patent number
US03944675

Reaction notes

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