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

HRID 749290ノート

反応式

HRID 749290 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e69ddf4a7f9943929943e6deea27467a
出典データセット
uspto-grants-2008_07
特許番号
US07402605B2

反応ノート

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