Methyl iodide → HCID 21483886, compound

HRID 1415213Notes

Reaction equation

HRID 1415213 reaction equation
[CH:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[C:9]([CH3:19])[C:10]([CH3:18])=[C:11]([O:16][CH3:17])[CH:12]=3)[C:7]2=[O:20])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:21]C(C)([O-])C.[K+].CI>C(O)(C)(C)C>[CH:1]1([C:6]2([CH3:21])[CH2:15][CH2:14][C:13]3[C:8](=[C:9]([CH3:19])[C:10]([CH3:18])=[C:11]([O:16][CH3:17])[CH:12]=3)[C:7]2=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 21483942HCID 21483942, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21483886HCID 21483886, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Conditions

Temperature
20 °C

Procedure

2-Cyclopentyl-6-methoxy-7,8-dimethyl-1-tetralone (Example V, Step 4) (12.5 g., 0.046 mole) is dissolved in t-butyl alcohol (250 ml.) under a stream of nitrogen. The mixture is heated to reflux and then a solution of potassium t-butoxide (7.5 g., 0.067 mole) dissolved in t-butyl alcohol (175 ml.) is added. The dark solution is refluxed for 1 hour, cooled to 20° C. and methyl iodide (14.2 g., 0.1 mole) is added. The mixture is refluxed for 10 minutes. Potassium iodide precipitates and the color of the mixture becomes lighter. The mixture is cooled, water (25 ml.) is added and the mixture is evaporated to dryness. The crude product is collected, washed with water and air dried to obtain 2-cyclopentyl-2,7,8-trimethyl-6-methoxy-1-tetralone.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. additionis added
  4. temperatureThe dark solution is refluxed for 1 hour
  5. temperatureThe mixture is refluxed for 10 minutes
  6. customPotassium iodide precipitates
  7. temperatureThe mixture is cooled
  8. additionwater (25 ml.) is added
  9. customthe mixture is evaporated to dryness
  10. customThe crude product is collected
  11. washwashed with water and air
  12. customdried

Sources & evidence

ORD record
ord-269c32aa25ea4133814f179b48f7e907
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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