Methyl iodide → HCID 56989563, compound

HRID 443097Notes

Reaction equation

HRID 443097 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:13])[CH:10]=[C:9]([CH3:11])[CH2:8][CH2:7][CH:6]([OH:12])[CH2:5]1.I[CH3:15]>C1(C)C=CC=CC=1>[CH3:15][O:12][CH:6]1[CH2:7][CH2:8][C:9]([CH3:11])=[CH:10][C:4]([CH3:13])([CH3:3])[CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11804986HCID 11804986, compound

Product 1

HCID 56989563HCID 56989563, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
98 °C

Procedure

Sodium hydride (60% in mineral oil) (5.4 gm) was added to 60 gm toluene in a stirred reaction flask and stirred under nitrogen. 3,3,5-Trimethyl-4-cyclohepten-1-ol (15.4 gm) was then added over 10 minutes at room temperature and stirred overnight. Iodomethane (21.3 gm) was added dropwise over 10 minutes followed by heating at 45° C. for six hours and four hours at 98° C. The reaction mixture was washed with 50 mL of saturated sodium bicarbonate solution and distilled through a short Vigreux column. A heart cut fraction, 3,3,5-trimethyl-4-cyclohepten-1-yl methyl ether, was obtained that weighed 13.9 gm and had a boiling point of 85° C. at 10 mm pressure. Its GC purity was 97%. The fraction was evaluated for its odor quality and characterized as fresh, spicy, saffron-like, floral, (marigold)-herbaceous-woody-powerful.

Workup

  1. stirringstirred overnight
  2. washThe reaction mixture was washed with 50 mL of saturated sodium bicarbonate solution
  3. distillationdistilled through a short Vigreux column

Sources & evidence

ORD record
ord-d9c5be1128fc4ecf97c1483b1161af68
Source dataset
uspto-grants-1999_04
Patent number
US05892104

Reaction notes

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