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

HRID 451586Notes

Reaction equation

HRID 451586 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].[Cl-].[Al+3].[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

A solution of tert-butyl benzene (31 ml, 200 mmol) and 3-chloro-propionyl chloride (19 ml, 200 mmol) in methylene chloride (75 ml) was added dropwise to a suspension of aluminum chloride (29.33 g, 220 mmol) in methylene chloride (300 ml) at 0° C. The reaction mixture was allowed to warm to ambient temperature, stirred for 16 hours, and quenched with water dropwise. The reaction mixture was washed with water, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step.

Workup

  1. customquenched with water dropwise
  2. washThe reaction mixture was washed with water
  3. dry with materialdried with magnesium sulfate
  4. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7f8c1ddce9324416948b80158610dc3a
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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