Sulfuric Acid → HCID 21547115, compound

HRID 1605668Notes

Reaction equation

HRID 1605668 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:18])[CH2:14][C:15](N)=[O:16])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][Mg]I.[Mg].CI.S(=O)(=O)(O)O>C(Cl)Cl.CCOCC>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH3:18])[CH2:14][C:15](=[O:16])[CH3:19])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 21547153HCID 21547153, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 21547115HCID 21547115, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 24.54 gm (0.1 mol) of 3-(4-cyclohexylphenyl)-butyramide in 750 ml of dry methylene chloride was added dropwise within one hour to a methyl magnesium iodide solution, prepared from 12.2 gm (0.5 mol) of magnesium and 71 gm (0.5 mol) of methyl iodide in a total of 400 ml of anhydrous ether, and, to complete the reaction, the resulting mixture was refluxed for 6 hours. The cooled mixture was then stirred into a mixture of 2 kg of ice and 100 ml of concentrated sulfuric acid. The organic phase was separated and washed twice with water, then with a saturated aqueous sodium bicarbonate solution and finally once more with water, then dried over anhydrous magnesium sulfate and concentrated by evaporation in vacuo. The residue was chroomatographically purified on 800 gm of silicagel, using benzene as the eluant, and the evaporated eluates were finally distilled in vacuo. 19.8 gm (81% of theory) of colorless oil, b.p. 104°-106°C at 0.05 mm Hg were obtained.

Workup

  1. customthe reaction
  2. temperaturethe resulting mixture was refluxed for 6 hours
  3. customThe organic phase was separated
  4. washwashed twice with water
  5. dry with materialwith a saturated aqueous sodium bicarbonate solution and finally once more with water, then dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe residue was chroomatographically purified on 800 gm of silicagel
  8. distillationthe evaporated eluates were finally distilled in vacuo
  9. custom19.8 gm (81% of theory) of colorless oil, b.p. 104°-106°C at 0.05 mm Hg were obtained

Sources & evidence

ORD record
ord-93d9cab4b2834c0d9e443cc5a340f999
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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