N,N-Dimethylaniline → 3',5'-Dimethoxybenzoin acrylate

HRID 2417746

반응식

HRID 2417746 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[CH:6]([OH:15])[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C1C=CC=CC=1.C(Cl)(=[O:33])C=C>C(Cl)Cl>[C:17]([OH:19])(=[O:33])[CH:16]=[CH2:5].[CH3:20][O:19][C:17]1[CH:16]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:18]=1)[CH:6]([OH:15])[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 949N,N-DimethylanilineHCID 13140Acryloyl chlorideHCID 5555932-(3,5-Dimethoxyphenyl)-2-hydroxy-1-phenyl-ethanone2회

생성물 1

HCID 703486503',5'-Dimethoxybenzoin acrylate수율 118.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To an ice cooled solution of 0.8 g (2.94 mmoles) of 3',5'-dimethoxybenzoin prepared in (3) above and 1.13 ml dimethylaniline in 10 ml methylene chloride, under nitrogen, was slowly added a solution of 1.5 ml (18 mmoles) acryloyl chloride in 10 ml of mehtylene chloride. After the addition was complete, the mixture was stirred overnight at room temperature, diluted with methylene chloride, washed twice with 75 ml 5% aqueous HCl, once with 100 ml H2O, once with 100 ml 5% aqueous NaHCO3, once with 100 ml H2O, once with 100 ml saturated Na2SO4 and dried over anhydrous Na2SO4. The solvent was filtered and stripped off to yield an oil that crystallized to give 0.6 g (63%) of compound. Recrystalization from benzene/hexane (1/1) gave colorless crystals, mp 88°-89° C. Infrared, NMR, and mass spectrometric analyses showed that the above compound was obtained.

후처리

  1. additionAfter the addition
  2. washwashed twice with 75 ml 5% aqueous HCl, once with 100 ml H2O, once with 100 ml 5% aqueous NaHCO3, once with 100 ml H2O, once with 100 ml saturated Na2SO4
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationThe solvent was filtered
  5. customto yield an oil that
  6. customcrystallized

출처 및 근거

ORD 기록
ord-f7d98038cb4b4dee9d93890febf7af69
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04469774

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