Sulfuric Acid → 1-Diethylamino-6-(m-methoxyphenyl)heptan-3-one
Reaction equation
[CH2:1]([N:3]([CH2:19][CH3:20])[CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH3:10])[CH3:2].S(=O)(=O)(O)[OH:22]>>[CH2:19]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6](=[O:22])[CH2:7][CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH3:10])[CH3:20]Participants
3
Procedure
Dissolve 1-diethylamino-6-(m-methoxyphenyl)hept-2-yne (13.6 g) in 10% aqueous sulphuric acid (40 cc) and stir with mercuric sulphate (0.69 g) for 2 hours at 70°. Filter the cooled solution, make basic with 10% aqueous sodium hydroxide and extract with ether. Wash the ethereal solution with water and brine, and dry (Na2SO4). Evaporate the solvent and distil the residue to obtain 1-diethylamino-6-(m-methoxyphenyl)heptan-3-one which has partially eliminated to 6-(m-methoxyphenyl)hept-1-en-3-one during the distillation, b.p. 145°/12 mm Hg.
Workup
- filtrationFilter the cooled solution
- extractionextract with ether
- washWash the ethereal solution with water and brine
- dry with materialdry (Na2SO4)
- customEvaporate the solvent
- customdistil the residue
Sources & evidence
- ORD record
- ord-a67a1a592125445e9d9bb445aa356d33
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03959322
Reaction notes
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