Acetyl chloride → 1-[2-Hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone

HRID 880357

반응식

HRID 880357 반응식
[CH3:1][O:2][CH2:3][O:4][CH3:5].[C:6](Cl)(=[O:8])C.[OH:10][C:11]1[CH:16]=C(O)[CH:14]=[C:13]([OH:18])[C:12]=1[C:19](=[O:21])[CH3:20].[CH3:22]CN(C(C)C)C(C)C>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[OH:18][C:13]1[CH:14]=[C:1]([O:2][CH2:3][O:4][CH3:5])[CH:16]=[C:11]([O:10][CH2:22][O:8][CH3:6])[C:12]=1[C:19](=[O:21])[CH3:20]

참가 물질

7

반응물 4

HCID 6367Acetyl chlorideHCID 8020DimethoxymethaneHCID 680732',4',6'-TrihydroxyacetophenoneHCID 81531Diisopropylethylamine

생성물 1

HCID 108796971-[2-Hydroxy-4,6-bis(methoxymethoxy)phenyl]ethanone

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 6344Dichloromethane용매2회

반응 조건

온도
20 °C

실험 절차

To a stirred solution of dimethoxymethane (66 mL, 745 mmol) and zinc bromide (0.5 g) in DCM (580 mL) was added drop wise acetyl chloride (53 mL, 745 mmol) during half an hour maintaining the temperature under 20° C. After stirring 3 hours at room temperature, the solution was diluted with DCM (1200 mL), then cooled at 5° C. before the portion wise addition of 1-(2,4,6-trihydroxyphenyl)ethanone (phloroacetophenone) (50 g, 208 mmol) followed by the drop wise addition of DIPEA (208 mL, 1.19 mol). The resulting cloudy solution was stirred overnight, and then was washed with a NH4Cl saturated solution followed by washing with 10% citric acid solution. After drying over Na2SO4, the solvent was removed and the residue (78 g) nearly pure was used for the next step.

후처리

  1. stirringThe resulting cloudy solution was stirred overnight
  2. washwas washed with a NH4Cl saturated solution
  3. washby washing with 10% citric acid solution
  4. dry with materialAfter drying over Na2SO4
  5. customthe solvent was removed

출처 및 근거

ORD 기록
ord-3d4961c3bbe247598c5fa49d7cd8b6fa
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993556B2

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