Acetic Acid → 4'-Chloro-2-methoxychalcone

HRID 1478237ノート

反応式

HRID 1478237 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 53462324'-Chloro-2-methoxychalcone収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fada9e3626de4864b3bcbec64f9fd4c3
出典データセット
uspto-grants-2016_08
特許番号
US09403827B2

反応ノート

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