Hydrochloric Acid → Ethanone, 1-(4-(4-(methylsulfonyl)phenoxy)phenyl)-

HRID 2164627Notes

Reaction equation

HRID 2164627 reaction equation
[CH3:1][S:2]([C:5]1[CH:17]=[CH:16][C:8]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:18](Cl)(=[O:20])[CH3:19].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:17]=[CH:16][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:18](=[O:20])[CH3:19])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 130785151-(Methanesulfonyl)-4-phenoxybenzene

Product 1

HCID 514879Ethanone, 1-(4-(4-(methylsulfonyl)phenoxy)phenyl)-Yield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.0 g (0.0202 mole) of 1-(4-(methylsulfonyl)phenoxy)benzene and 2.20 g (0.0280 mole) of acetyl chloride dissolved in 35 ml of methylene chloride (CH2Cl2) was slowly added 6.70 g (0.0503 mole) of anhydrous aluminum chloride. The mixture was heated at reflux for 45 minutes, cooled and poured over ice and concentrated hydrochloric acid (conc. HCl). Additional CH2Cl2 was added and the organic layer separated, washed with water and dried (Na2SO4). Removal of solvent in vacuo yielded 5.2 g (88.9% yield) of purified 1-(4-(4-(methylsulfonyl)phenoxy)phenyl)ethanone, mp 131°-132.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 45 minutes
  3. temperaturecooled
  4. customthe organic layer separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-b6dee222ce2040e2ae0f96cc425f0002
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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