Tert-Butylbenzene → 1-(4-T-Butylphenyl)-3-chloropropan-1-one

HRID 237266Notes

Reaction equation

HRID 237266 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:11][CH2:12][CH2:13][C:14](Cl)=[O:15].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:14](=[O:15])[CH2:13][CH2:12][Cl:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7366Tert-ButylbenzeneHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 222283931-(4-T-Butylphenyl)-3-chloropropan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl benzene (1.0 g, 7.5 mmol) and 3-chloropropionyl chloride (0.7 mL, 7.5 mmoL) in CH2Cl2 (20 mL) was added dropwise to a suspension of AlCl3 (1.1 g, 8.2 mmol) in CH2Cl2 (10 mL) at 0° C. The reaction was allowed to warm to rt. After 15 h, the reaction was quenched with H2O (10 mL) and extracted with CH2Cl2 (2×20 mL). The organic layers were combined and dried to give the title compound that was used without further purification (1.3 g).

Workup

  1. customthe reaction was quenched with H2O (10 mL)
  2. extractionextracted with CH2Cl2 (2×20 mL)
  3. customdried

Sources & evidence

ORD record
ord-d0b465b69b154d308bdf2b1dce9959ce
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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