Methanol → Methanone, [4-(methoxymethyl)phenyl]phenyl-

HRID 2049905Notes

Reaction equation

HRID 2049905 reaction equation
[OH-:1].[K+].Cl[CH2:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.[CH3:19]O>>[CH3:19][O:1][CH2:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 30163764-(Chloromethyl)benzophenone

Product 1

HCID 111774Methanone, [4-(methoxymethyl)phenyl]phenyl-Yield 88.5%

Procedure

To 4 liters of absolute methyl alcohol was added 300 grams (4.5 moles) of 85% potassium hydroxide pellets with mechanical stirring. The amount of 618 grams (2.7 moles) of 4-(chloromethyl)benzophenone was added to the resulting warm solution. The reaction mixture was refluxed for three hours, filtered with suction, and concentrated. Water was added and the lower oily layer was separated and distilled to provide 530 grams (88.5% yield) of 4-(methoxymethyl)benzophenone as an almost colorless liquid (b.p. 140° C., 0.20 mm Hg). The infrared spectrum revealed a carbonyl band at 1660 cm-1. Ultraviolet analysis revealed λ max (ε) at 256 nanometers (18,380).

Workup

  1. temperaturewarm solution
  2. temperatureThe reaction mixture was refluxed for three hours
  3. filtrationfiltered with suction
  4. concentrationconcentrated
  5. additionWater was added
  6. customthe lower oily layer was separated
  7. distillationdistilled

Sources & evidence

ORD record
ord-d6f35dde5676480ebece24b69144e9d8
Source dataset
uspto-grants-1980_04
Patent number
US04199420

Reaction notes

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