Chromate → Bis(3,5-dimethoxyphenyl)methanone

HRID 883827

반응식

HRID 883827 반응식
[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

참가 물질

6

반응물 3

HCID 24461ChromateHCID 67173126Bis(3,5-dimethoxyphenyl)methanol2회HCID 178418287HCID 178418287, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-911afee0ea70455fa675b44eb38baa0f
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08237003B2

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