Methyl iodide → HCID 914776, compound

HRID 1657043Notes

Reaction equation

HRID 1657043 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]=[C:7]2[CH2:12][CH2:11][CH2:10][CH:9]([CH3:13])[C:8]2=[O:14])=[CH:4][CH:3]=1.CI.[C:19](O)(CC)(C)C.[H-].[Na+]>O.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[C:7]2[CH2:12][CH2:11][CH2:10][C:9]([CH3:19])([CH3:13])[C:8]2=[O:14])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 64052-Methyl-2-butanolHCID 24758Sodium hydrideHCID 3259543HCID 3259543, compound

Product 1

HCID 914776HCID 914776, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

2-(4-Chlorobenzylidene)-6-methylcyclohexanone (7.0 g), prepared above, and then methyl iodide (5.1 g) are added successively to a reaction medium prepared from toluene (25 cc), tert-amyl alcohol (3.6 cc) and sodium hydride (1.35 g of 60% strength dispersion in oil) and heated to 45° C. The mixture is brought to reflux (1 h), poured into water and extracted with ethyl acetate. After drying and concentration, the residue is recrystallized in methanol to give 2-(4-chlorobenzylidene)-6,6-dimethylcyclohexanone (4.7 g), m.p. 92°.

Workup

  1. additionare added successively to a reaction medium
  2. temperatureto reflux (1 h)
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. concentrationconcentration
  6. customthe residue is recrystallized in methanol

Sources & evidence

ORD record
ord-7eacf55283f440a49a116469cfd58602
Source dataset
uspto-grants-1993_10
Patent number
US05256683

Reaction notes

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