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

HRID 1276135노트

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HRID 1276135 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e5a093efc0e6483e94f31f84b4b8af55
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06165944

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