Chromate → Bis(3,5-dimethoxyphenyl)methanone

HRID 883827

反応式

HRID 883827 の反応式
[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

参加物

6

反応物 3

HCID 24461ChromateHCID 67173126Bis(3,5-dimethoxyphenyl)methanol2 回HCID 178418287HCID 178418287、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-911afee0ea70455fa675b44eb38baa0f
出典データセット
uspto-grants-2012_08
特許番号
US08237003B2

関連ノート

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