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

HRID 913233Notes

Reaction equation

HRID 913233 reaction equation
[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]

Participants

6

Reactant 5

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

Product 1

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

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8f13853d7c36447ea3e6d4b13ee7a933
Source dataset
uspto-grants-2011_09
Patent number
US08026273B2

Reaction notes

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