Ethanol → Methanone, [4-(ethoxymethyl)phenyl]phenyl-

HRID 2049906Notes

Reaction equation

HRID 2049906 reaction equation
[OH-].[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.[CH2:19]([OH:21])[CH3:20]>>[CH2:19]([O:21][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)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 30163764-(Chloromethyl)benzophenone

Product 1

HCID 3085642Methanone, [4-(ethoxymethyl)phenyl]phenyl-Yield 84%

Procedure

To 1 liter of absolute ethyl alcohol was added 80 grams (1.2 moles) of 85% potassium hydroxide pellets with mechanical stirring. The amount of 115 grams (0.5 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 102 grams (84% yield) of 4-(ethoxymethyl)benzophenone. Infrared analysis revealed the presence of a carbonyl band at 1660 cm-1. Ultraviolet analysis revealed λ max (ε) of 256 nanometers (18,360). Proton nuclear magnetic resonance analysis revealed the following where m is a multiplet, s is a singlet, q is a quartet, t is a triplet and TMS is tetramethylsilane.

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-f6486a021a194c1fb84d6b5dc050860a
Source dataset
uspto-grants-1980_04
Patent number
US04199420

Reaction notes

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