Sulfuric Acid → 5-Methyl-6-(m-methoxyphenyl)hex-1-en-3-one

HRID 1414950Notes

Reaction equation

HRID 1414950 reaction equation
C(N(CC)[CH2:4][C:5]#[C:6][CH2:7][CH:8]([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)C.S(=O)(=O)(O)[OH:22]>O>[CH3:18][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH2:7][C:6](=[O:22])[CH:5]=[CH2:4]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 214854231-Diethylamino-5-methyl-6-(m-methoxyphenyl)hex-2-yne

Product 1

HCID 214854785-Methyl-6-(m-methoxyphenyl)hex-1-en-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add mercuric sulphate (0.45 g) to a stirred solution of 1-diethylamino-5-methyl-6-(m-methoxyphenyl)hex-2-yne (8 g) in concentrated sulfuric acid (2.5 cc) and water (25 cc) and heat the mixture at 70° for 11/2 hours. Filter the cooled solution, make basic with 10% aqueous sodium hydroxide and extract with ether. Wash and dry the ethereal solution and evaporate to leave as residue crude 1-diethylamino-6-(m-methoxyphenyl)-5-methylhexan-3-one; infrared absorption peaks at 5.85 μ. Slowly distil at 0.1 mm Hg to obtain 5-methyl-6-(m-methoxyphenyl)hex-1-en-3-one; infrared absorption peaks at 5.85 μ.

Workup

  1. temperatureheat the mixture at 70° for 11/2 hours
  2. filtrationFilter the cooled solution
  3. extractionextract with ether
  4. washWash
  5. customdry the ethereal solution
  6. customevaporate
  7. customto leave as residue crude 1-diethylamino-6-(m-methoxyphenyl)-5-methylhexan-3-one
  8. custominfrared absorption peaks at 5.85 μ
  9. customSlowly distil at 0.1 mm Hg

Sources & evidence

ORD record
ord-f88701bf15ad44f9a38d75508342a540
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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