Hydrochloric Acid → AD 2239

HRID 370741Notes

Reaction equation

HRID 370741 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:14])[CH2:12][CH3:13].[CH2:15]=O.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[ClH:22]>C(O)(C)C.CC(C)=O>[ClH:22].[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:14])[CH:12]([CH3:15])[CH2:13][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 31268PyrrolidineHCID 133066961-Propanone, 1-(4-methoxy-2,3-dimethylphenyl)-

Product 1

HCID 146238AD 2239

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

1-(2,3-Dimethyl-4-methoxyphenyl)-1-propanone (20.0 g), paraformaldehyde (6.2 g) and pyrrolidine (8.9 g) are combined in isopropanol (30 ml) and 35% ethanolic hydrogen chloride (16 ml) is added to adjust the solution to an acidic pH. The mixture is then stirred and heated at reflux for 20 hours. After cooling, acetone (300 ml) is added to the reaction mixture and the resulting solution is cooled in ice water. Crystalline product is filtered and recrystallized twice from ethanol (50 ml)-acetone (50 ml) to give the analytically pure title compound (10.0 g), m.p. 169°-172° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. filtrationCrystalline product is filtered
  5. customrecrystallized twice from ethanol (50 ml)-acetone (50 ml)

Sources & evidence

ORD record
ord-681fe562a1044dd6a2987c2987ec7ad0
Source dataset
uspto-grants-1985_07
Patent number
US04528299

Reaction notes

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