Methyl iodide → HCID 53760314, compound

HRID 67273

Reaction equation

HRID 67273 reaction equation
[Mg].I[CH3:3].[C:4]1(=[O:19])[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=[CH:5]1.[Cl-].[NH4+]>CCOCC>[CH3:3][CH:17]1[CH2:18][C:4](=[O:19])[CH:5]=[CH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 53676690Cyclopentadeca-2,14-dien-1-one

Product 1

HCID 53760314HCID 53760314, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the Grignard reagent prepared from 72 mg (3 mg-atoms) of magnesium and 0.25 ml (4 mMole) of iodomethane in 5 ml of ether was added 50 mg of cuprous iodide, and the mixture was heated at reflux for 5 min. Cyclopentadeca-2,14-dien-1-one (0.44 g; 2 mMole) in 5 ml of ether was then added over a period of 10 min without cooling, and stirring was continued for 30 min at room temperature. The reaction mixture was poured into cold ammonium chloride solution and extracted with ether. The organic layer was washed with water, dried over sodium sulphate, evaporated and distilled to give 0.33 g (69%) of dehydromuscone having b.p. 110°/0.1 Torr;

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 5 min
  3. temperaturewithout cooling
  4. extractionextracted with ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. distillationdistilled
  9. customto give 0.33 g (69%) of dehydromuscone

Sources & evidence

ORD record
ord-dd6afe4503ee4664908ebec4744ca981
Source dataset
uspto-grants-1982_08
Patent number
US04346023

Linked notes

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