Iodoethane → HCID 57044892, compound

HRID 443098Notes

Reaction equation

HRID 443098 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[CH2:15][CH3:16]>C1(C)C=CC=CC=1>[CH2:15]([O:12][C:6]1[CH2:7][CH2:8][CH:9]([CH3:11])[CH2:10][C:4]([CH3:13])([CH3:3])[CH:5]=1)[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11804986HCID 11804986, compound

Product 1

HCID 57044892HCID 57044892, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
72 °C

Procedure

Sodium hydride (60% in mineral oil) (5.4 gm) was added to 60 gm toluene in a reaction flask and stirred under nitrogen. 3,3,5-Trimethyl-4-cyclohepten-1-ol (15.4 gm) was added over 10 minutes at room temperature and stirred for 25 minutes. Iodoethane (23.4 gm) was next added over five minutes. The reaction was heated to 72° C. over 1.5 hours and then four hours at 112° C. The crude oil was washed once with 50 mL saturated sodium bicarbonate solution and distilled through a short Vigreux column. A heart cut fraction, 3,3,5-trimethyl-cyclohepten-1-yl ethyl ether, was obtained that weighed 14.9 gm and had a boiling point of 89° C. at 10 mm pressure. Its GC purity was 94%. The fraction was evaluated for its odor quality and characterized as having fresh diffusive citrus lime notes as well as fruity-peach/prune-rose floral.

Workup

  1. stirringstirred for 25 minutes
  2. customfour hours
  3. customat 112° C
  4. washThe crude oil was washed once with 50 mL saturated sodium bicarbonate solution
  5. distillationdistilled through a short Vigreux column

Sources & evidence

ORD record
ord-a446560bf6e34cb9998e551325415372
Source dataset
uspto-grants-1999_04
Patent number
US05892104

Reaction notes

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