Chromate → Bis(3,5-dimethoxyphenyl)methanone

HRID 2407596

Reaction equation

HRID 2407596 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:22]([C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[CH:25]=2)[OH:23])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1.[Cr]([O-])([O-])(=O)=O>ClCCl.CCOCC>[CH3:33][O:32][C:26]1[CH:25]=[C:24]([C:22]([C:16]2[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)=[O:23])[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=1

Participants

6

Reactant 3

HCID 24461ChromateHCID 67173126Bis(3,5-dimethoxyphenyl)methanol2×HCID 178418287HCID 178418287, compound

Product 1

HCID 21609692Bis(3,5-dimethoxyphenyl)methanoneYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (PCC) (12.9 g, 30 mmol) was suspended in 30 mL dichloromethane in a 200 mL round bottom flask. Crude bis(3,5-dimethoxyphenyl)methanol from above (compound A) was suspended in 30 mL dichloromethane then added to the chromate suspension. The dark solution was allowed to stir at ambient temperature for 18 hours then diluted with ether. After decantation, the organic solution was washed twice with 1N NaOH, twice with 10% HCl, saturated NaHCO3, and then with brine. It was dried over anhydrous MgSO4, filtered and concentrated to give a brownish yellow solid. The brownish yellow solid was purified by column chromatography using 50% acetone/hexane as eluent giving the product as a yellow solid in 63% yield over 2 steps: IR (cm−1): 2960, 2938, 2834, 1660, 1592, 1456, 1425, 1349, 1304, 1205, 1157, 1066, 744; 1H NMR (250 MHz, C6D6): δ 3.21 (s, 12H), 6.67 (t, J=2.2 Hz, 2H), 7.21 (d, J=2.5 Hz, 4H); 13C NMR (63 MHz, C6D6): 54.9 (4C), 105.3 (2C), 108.0 (4C), 140.2 (2C), 161.1 (4C), 195.2.

Workup

  1. washAfter decantation, the organic solution was washed twice with 1N NaOH, twice with 10% HCl, saturated NaHCO3
  2. dry with materialIt was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a brownish yellow solid
  6. customThe brownish yellow solid was purified by column chromatography

Sources & evidence

ORD record
ord-0a3759ea67f14fd09be2e1532ccd1b69
Source dataset
uspto-grants-2014_08
Patent number
US08809563B2

Linked notes

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