Acetic Acid → 4'-Chloro-2-methoxychalcone

HRID 1478237노트

반응식

HRID 1478237 반응식
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.CC(O)=O>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])/[CH:11]=[CH:17]/[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[O:14][CH3:13])=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7467P-ChloroacetophenoneHCID 86582-MethoxybenzaldehydeHCID 14797Potassium Hydroxide

생성물 1

HCID 53462324'-Chloro-2-methoxychalcone수율 97%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

KOH (1.415 g, 25.2 mmol) was added to a solution of 1-(4-chlorophenyl)ethanone (3.9 g, 25.2 mmol) and 2-methoxybenzaldehyde (3.43 g, 25.2 mmol) in methanol (100 ml) at RT and the solution was stirred for 18 hours. The solution was concentrated under reduced pressure until a precipitate was formed. AcOH (1.444 ml, 25.2 mmol) was added and the mixture was cooled down to 0° C.-5° C. The mixture was stirred for 1 hour and the light yellow precipitate was separated by filtration and washed with cold methanol to afford 6.72 g (24.39 mmol, 97% yield) of the title compound. LCMS: (M+H)=273; tR=1.28 min (LC-MS 3). 1H-NMR (d6-DMSO, 600 MHz) δ ppm 8.12 (d, 2H) 8.04 (d, 1H) 7.98 (d, 1H) 7.86 (d, 1H) 7.62 (d, 2H) 7.45 (t, 1H) 7.10 (d, 1H) 7.02 (t, 1H) 3.88 (s, 3H).

후처리

  1. concentrationThe solution was concentrated under reduced pressure until a precipitate
  2. customwas formed
  3. temperaturethe mixture was cooled down to 0° C.-5° C
  4. stirringThe mixture was stirred for 1 hour
  5. customthe light yellow precipitate was separated by filtration
  6. washwashed with cold methanol

출처 및 근거

ORD 기록
ord-fada9e3626de4864b3bcbec64f9fd4c3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403827B2

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