Dimethyl Sulfoxide → 2-Methoxymethoxy-3-methyl-2'-methoxybenzophenone

HRID 466930Notes

Reaction equation

HRID 466930 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[O:28][CH2:29][O:30][CH3:31])[OH:20].C(N(CC)CC)C>ClCCl>[CH3:31][O:30][CH2:29][O:28][C:22]1[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:21]=1[C:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][CH3:11])=[O:20]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19812676(2-Methoxyphenyl)(3-methyl-2-methoxymethoxyphenyl)methanol

Product 1

HCID 198126582-Methoxymethoxy-3-methyl-2'-methoxybenzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 8.72 ml of oxalyl chloride in 300 ml of dichloromethane was cooled with a dry ice-acetone bath and a solution of 13.9 ml of dimethyl sulfoxide in 50 ml of dichloromethane was added dropwise with stirring. After 30 min, (2-methoxyphenyl)(3-methyl-2-methoxymethoxyphenyl)methanol (26.4 g) dissolved in 100 ml of dichloromethane was added slowly with stirring and the mixture allowed to react for 1 hour. Triethylamine (64 ml) was then added and the resulting mixture was stirred another 30 min cold and then allowed to warm to room temperature. The product mixture was extracted sequentially with water, 5 percent hydrochloric acid, water, and 5 percent sodium carbonate. It was then dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain an oil. This was purified by preparative liquid chromatography to obtain the title compound as an oil. The assigned structure was consistent with the proton NMR spectrum.

Workup

  1. additionwas added slowly
  2. stirringwith stirring
  3. customto react for 1 hour
  4. stirringthe resulting mixture was stirred another 30 min cold
  5. extractionThe product mixture was extracted sequentially with water, 5 percent hydrochloric acid, water, and 5 percent sodium carbonate
  6. dry with materialIt was then dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customto obtain an oil
  10. customThis was purified by preparative liquid chromatography

Sources & evidence

ORD record
ord-96917fa44cd341b1b520e4fc965b01b8
Source dataset
uspto-grants-1992_10
Patent number
US05158597

Reaction notes

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