Methyl iodide → HCID 15617899, compound

HRID 1165016Notes

Reaction equation

HRID 1165016 reaction equation
[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[OH:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[C:21](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]1([CH2:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[O:18][CH3:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 160268Dup 654

Product 1

HCID 15617899HCID 15617899, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-phenylmethyl-1-naphthol (40.0 g, 0.17 mole), methyl iodide (36.4 g, 0.26 mole), potassium carbonate (35.9 g, 0.26 mole) and acetone (1000 mL) was heated at reflux with stirring for 17 hours, then cooled and filtered. The acetone was removed under vacuum, and the residue was dissolved in ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated. The residual oil was distilled in a short-path distillation apparatus at approximately 160°-180°/0.2 torr to provide the title compound (41.5 g, 98%) as an off-white solid, mp 56°-59°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe acetone was removed under vacuum
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. distillationThe residual oil was distilled in a short-path distillation apparatus at approximately 160°-180°/0.2 torr

Sources & evidence

ORD record
ord-297faa89f5314006b84cb2bfc183023e
Source dataset
uspto-grants-1990_03
Patent number
US04906636

Reaction notes

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