Methyl iodide → HCID 21495610, compound

HRID 1731189Notes

Reaction equation

HRID 1731189 reaction equation
[OH:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:20][O:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223484(4-Chlorophenyl)(2-hydroxy-3-methylphenyl)methanone

Product 1

HCID 21495610HCID 21495610, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 195.9 g of 2-hydroxy-3-methyl-4'-chlorobenzophenone [Huston et al., JACS, Vol. 73, (1951), p. 2483] in 1 liter of dimethylformamide was added with stirring to a suspension of 40.8 g of sodium hydride in 200 ml of dimethylformamide and the mixture was stirred for 1 hour with cooling in an ice-water bath. Then, a solution of 170.4 g of methyl iodide in 800 ml of dimethylformamide was added thereto over 40 minutes and the mixture was then stirred for 16 hours in the ice-water bath. The mixture was filtered to remove insolubles and the filtrate was treated with activated carbon, filtered and was evaporated to dryness under reduced pressure. The residue was taken up in 1 liter of ether and 200 ml of water and the aqueous phase was reextracted with ether. The combined ether phases were washed with water, dried over magnesium sulfate, treated with activated carbon, filtered and evaporated to dryness. The residue was chromatographed over silica and was eluted with methylene chloride to obtain 171 g of 2-methoxy-3-methyl-4'-chlorobenzophenone in the form of colorless crystals melting at 43° C.

Workup

  1. temperaturewith cooling in an ice-water bath
  2. waitover 40 minutes
  3. filtrationThe mixture was filtered
  4. customto remove insolubles
  5. additionthe filtrate was treated with activated carbon
  6. filtrationfiltered
  7. customwas evaporated to dryness under reduced pressure
  8. washThe combined ether phases were washed with water
  9. dry with materialdried over magnesium sulfate
  10. additiontreated with activated carbon
  11. filtrationfiltered
  12. customevaporated to dryness
  13. customThe residue was chromatographed over silica
  14. washwas eluted with methylene chloride

Sources & evidence

ORD record
ord-cf225572ac34404aaa11efabda7aa39d
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

Loading…