Sulfuric Acid → 1-Diethylamino-6-(m-methoxyphenyl)heptan-3-one

HRID 1414949Notes

Reaction equation

HRID 1414949 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

Reactant 2

HCID 1118Sulfuric AcidHCID 214856761-Diethylamino-6-(m-methoxyphenyl)hept-2-yne

Product 1

HCID 214857581-Diethylamino-6-(m-methoxyphenyl)heptan-3-one

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

  1. filtrationFilter the cooled solution
  2. extractionextract with ether
  3. washWash the ethereal solution with water and brine
  4. dry with materialdry (Na2SO4)
  5. customEvaporate the solvent
  6. customdistil the residue

Sources & evidence

ORD record
ord-58e097e77bc84ba4bfe6bb2e51ca2961
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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