Water → Methyl 2,4-dichloro-3-(2-oxobut-3-en-4-yl)benzoate

HRID 1276135ノート

反応式

HRID 1276135 の反応式
[CH3:1][C:2](C)([O-:4])[CH3:3].[K+].[Cl:7][C:8]1[C:17]([CH:18]=O)=[C:16]([Cl:20])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[Cl-].O=C(C)C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>O1CCCC1>[Cl:7][C:8]1[C:17]([CH:18]=[CH:1][C:2](=[O:4])[CH3:3])=[C:16]([Cl:20])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

参加物

6

反応物 4

HCID 962WaterHCID 196994Acetonyltriphenylphosphonium chlorideHCID 15430822Methyl 2,4-dichloro-3-formylbenzoateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 54401157Methyl 2,4-dichloro-3-(2-oxobut-3-en-4-yl)benzoate収率 88%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

At room temperature, first 14.0 g (125 mmol) of potassium t-butoxide and then, after 30 minutes, 23.3 g (100 mmol) of methyl 2,4-dichloro-3-formylbenzoate in 200 ml of tetrahydrofuran were added to 53.2 g (150 mmol) of (2-oxopropyl)triphenylphosphonium chloride in 300 ml of tetrahydrofuran. The mixture was stirred at room temperature for 4.5 hours and 400 ml of water were then added, the organic phase was separated off and the aqueous phase was extracted with methyl t-butyl ether. The combined organic phases were dried and concentrated and the resulting residue was chromatographed over silica gel (eluent: cyclohexane:ethyl acetate=9:1). 24.0 g (88% of theory) of methyl 2,4-dichloro-3-(2-oxobut-3-en-4-yl)benzoate were obtained.

後処理

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted with methyl t-butyl ether
  3. customThe combined organic phases were dried
  4. concentrationconcentrated
  5. customthe resulting residue was chromatographed over silica gel (eluent: cyclohexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-e5a093efc0e6483e94f31f84b4b8af55
出典データセット
uspto-grants-2000_12
特許番号
US06165944

反応ノート

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