Potassium Iodide → Ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate

HRID 26229

Reaction equation

HRID 26229 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C[O-].[Na+].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].[I-].[K+]>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([CH:10]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:16]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 89191-BromododecaneHCID 10942334Sodium MethoxideHCID 21325235Ethyl 4-(2-methylphenyl)-3-oxobutanoate

Product 1

HCID 21325239Ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Three parts of ethyl 4-(2-methylphenyl)-3-oxobutanoate, 1 part of sodium methoxide, 4.6 parts of 1-bromododecane, 0.5 parts of potassium iodide and 50 parts of absolute ethanol were refluxed together for 4 hours and then stirred 18 hours at room temperature. The mixture was evaporated to a small volume, diluted with 100 parts water and extracted with ether. The ether extract was washed with saturated sodium bicarbonate, saturated sodium chloride solution and dried over magnesium sulfate. Evaporation of the ether gave 6 parts of crude ethyl 2-[(2-methylphenyl)acetyl]tetradecanoate as an oil which was not further purified.

Workup

  1. customThe mixture was evaporated to a small volume
  2. additiondiluted with 100 parts water
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with saturated sodium bicarbonate, saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the ether

Sources & evidence

ORD record
ord-421a65b248de467d90087779c3476745
Source dataset
uspto-grants-1979_04
Patent number
US04148918

Linked notes

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