1,2-Dichloroethane → Ethyl 4-(4-tert-butylphenyl)-4-oxobutanoate

HRID 913233노트

반응식

HRID 913233 반응식
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].C([CH:17]([CH2:21][C:22](Cl)=[O:23])[C:18](Cl)=[O:19])C.[OH2:25].Cl[CH2:27][CH2:28]Cl>>[CH2:27]([O:25][C:22](=[O:23])[CH2:21][CH2:17][C:18](=[O:19])[C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)[CH3:28]

참가 물질

6

반응물 5

HCID 111,2-DichloroethaneHCID 962WaterHCID 7366Tert-ButylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 218646082-Ethylbutanedioyl dichloride

생성물 1

HCID 19700489Ethyl 4-(4-tert-butylphenyl)-4-oxobutanoate

실험 절차

To a solution of t-butylbenzene (2.00 g) in 1,2-dichloroethane (30 mL) was added aluminum chloride (2.2 g) in ice bath. Ethyl succinyl chloride (2.3 mL) was added dropwise to the mixture, which was stirred at room temperature for 23 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=9:1→5:1) to give the title compound (629 mg) having the following physical data.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=9:1→5:1)

출처 및 근거

ORD 기록
ord-8f13853d7c36447ea3e6d4b13ee7a933
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026273B2

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