Benzene → HCID 54171581, compound

HRID 1833492Notes

Reaction equation

HRID 1833492 reaction equation
[H-].[Na+].[CH:3]1C=CC=CC=1.[CH3:9][C:10]([OH:19])([CH2:12][CH2:13][CH:14]=[CH:15][C:16]([CH3:18])=[CH2:17])[CH3:11].CI>O>[CH3:3][O:19][C:10]([CH3:9])([CH2:12][CH2:13][CH:14]=[CH:15][C:16]([CH3:18])=[CH2:17])[CH3:11]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53748541HCID 53748541, compound

Product 1

HCID 54171581HCID 54171581, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.8 g (0.11 mol) of a 50% suspension of sodium hydride in paraffin oil are mixed with 120 ml of benzene in a three-necked flask provided with a thermometer, stirrer, reflux condenser and dropping funnel. 16.9 g of 2,7-dimethyl-5,7-octadien-2-ol are slowly added dropwise thereto. The reaction is completed by heating the mixture at reflux for 2 hours. 28 g (0.2 mol) of methyl iodide are then added dropwise at 30° C. After completion of the addition, the mixture is heated at reflux for 2 hours. After cooling, 50 ml of water are cautiously added. The benzene layer is separated and washed neutral with water. The solvent is distilled off and the residue fractionally distilled. There are obtained 13.7 g of 2-methoxy-2,7-dimethyl-5,7-octadiene of boiling point 72° C/3 mm Hg; nD20 = 1.4670; IR n° 24872 (s 1085 cm-1); NMR n° 23421 (3.17 ppm, 3 H, S, --O--CH3). Odor: natural, fresh, reminiscent of lavender; suitable in combination with esters.

Workup

  1. customprovided with a thermometer, stirrer
  2. temperaturereflux condenser
  3. temperatureby heating the mixture
  4. temperatureat reflux for 2 hours
  5. additionAfter completion of the addition
  6. temperaturethe mixture is heated
  7. temperatureat reflux for 2 hours
  8. temperatureAfter cooling
  9. customThe benzene layer is separated
  10. washwashed neutral with water
  11. distillationThe solvent is distilled off
  12. distillationthe residue fractionally distilled

Sources & evidence

ORD record
ord-1682b6491f114db3a8a393c0fa55c444
Source dataset
uspto-grants-1978_01
Patent number
US04066710

Reaction notes

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