Ammonium Chloride → 4-(2,6-Dimethylphenyl)-2-pentanone

HRID 1761515Notes

Reaction equation

HRID 1761515 reaction equation
[CH3:1][Li].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH:11]=[CH:12][C:13](=[O:15])[CH3:14].[NH4+].[Cl-]>O1CCCC1.[Cu]I>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH:11]([CH3:1])[CH2:12][C:13](=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 542926874-(2,6-Dimethylphenyl)-3-buten-2-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 212418864-(2,6-Dimethylphenyl)-2-pentanone

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture containing 20 g of CuI and 50 ml of tetrahydrofuran (THF) are added 105 ml of methyllithium dropwise during with agitation in a nitrogen atmosphere at a temperature of 0° C. or lower until the yellow precipitate barely dissolves. Then 8.7 g of 4-(2,6-dimethylphenyl)-3-buten-2-one in 50 ml of THF are added slowly at 0° C. The stirring is continued for an additional 2 h with a gradual increase of the temperature to +25° C. The reaction mixture obtained is hydrolysed with 300 ml of a solution of NH4Cl. The ether layer is removed, dried and evaporated to give the crude product.

Workup

  1. dissolutionlower until the yellow precipitate barely dissolves
  2. temperaturewith a gradual increase of the temperature to +25° C
  3. customThe reaction mixture obtained
  4. customThe ether layer is removed
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-5036e168db8541b7a717bf36f339bcd7
Source dataset
uspto-grants-1989_05
Patent number
US04826864

Reaction notes

Loading…