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

HRID 2223380Notes

Reaction equation

HRID 2223380 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-154bc62affa24a0b8593f4cca2019f80
Source dataset
uspto-grants-2008_05
Patent number
US07375126B2

Reaction notes

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