Thionyl Chloride → HCID 22325571, compound

HRID 496311Notes

Reaction equation

HRID 496311 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].S(Cl)(Cl)=O.[CH2:10]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[CH3:21])[CH2:11][CH3:12]>>[C:20]([C:15]1[CH:16]=[C:17]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:18]=[CH:19][C:14]=1[O:13][CH2:10][CH2:11][CH3:12])(=[O:22])[CH3:21]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 136295491-(2-propoxyphenyl)ethanone

Product 1

HCID 22325571HCID 22325571, compoundYield 81%

Conditions

Temperature
0 °C

Procedure

To a mixture of chlorosulphonic acid (27 mL) and thionyl chloride (3.6 mL) at 0° C. was added portionwise 1-(2-propoxyphenyl)ethanone (5.0 g, 28.1 mmol). The resulting mixture was stirred at 0° C. for 20 min. and at room temperature overnight, poured cautiously into ice-water and extracted with methylene chloride. The organic solution was washed sequentially with water, aqueous sodium bicarbonate and brine, dried (MgSO4), and the solvent removed under reduced pressure to yield the title compound (6.3 g, 81%) as an off-white solid.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic solution was washed sequentially with water, aqueous sodium bicarbonate and brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-43858716f21640c7baa21b5efe7724e3
Source dataset
uspto-grants-2005_09
Patent number
US06943253B2

Reaction notes

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