Sec-Butylbenzene → HCID 21328147, compound

HRID 1703582Notes

Reaction equation

HRID 1703582 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:17][CH3:18])[CH3:16]>[SH-].[C+4].[SH-].[SH-].[SH-]>[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[F:1])=[O:5])=[CH:21][CH:20]=1)([CH2:17][CH3:18])[CH3:16]

Participants

5

Reactant 3

HCID 8680Sec-ButylbenzeneHCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21328147HCID 21328147, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 178420937HCID 178420937, compoundSolvent

Procedure

A 3.17 g (0.02 mole) of 2-fluorobenzoic acid chloride was dissolved in 30 ml of carbon bisulfide and then, 3.99 g (0.03 mole) of anhydrous aluminum chloride was added to the solution. A 2.68 g (0.02 mole) of sec-butyl benzene was further added to the mixture with stirring and the reaction was carried out at room temperature for 18 hours. Carbon bisulfide was distilled off from the reaction mixture and water was added and the reaction product was extracted with benzene. The benzene phase was separated washed with 1N-NaOH and with water and was dried with anhydrous sodium sulfate. The solvent was distilled off to obtain a pale yellow oily product. The oily product was distilled under a reduced pressure to obtain 3.9 g of 4-sec-butyl-2'-fluorobenzophenone having a boiling point of 152° to 160° C./5 mmHg. (yield of 76.4%).

Workup

  1. distillationCarbon bisulfide was distilled off from the reaction mixture and water
  2. additionwas added
  3. extractionthe reaction product was extracted with benzene
  4. customThe benzene phase was separated
  5. washwashed with 1N-NaOH and with water
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain a pale yellow oily product
  9. distillationThe oily product was distilled under a reduced pressure

Sources & evidence

ORD record
ord-f6e3defd9488478ba368473e8232839e
Source dataset
uspto-grants-1978_11
Patent number
US04124726

Reaction notes

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