Hydrochloric Acid → 1-(5-Chloro-2,4-dimethoxyphenyl)ethan-1-one

HRID 2257123Notes

Reaction equation

HRID 2257123 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].[C:12](Cl)(=[O:14])[CH3:13].Cl>C(Cl)(Cl)(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[CH:4][C:5]([O:8][CH3:9])=[C:6]([C:12](=[O:14])[CH3:13])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 1389051-Chloro-2,4-dimethoxybenzene

Product 1

HCID 24325931-(5-Chloro-2,4-dimethoxyphenyl)ethan-1-oneYield 48.4%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2 g of 1-chloro-2,4-dimethoxybenzene and 0.9 g of acetyl chloride in 20 ml of CCl4 is cooled to 0° C., and a solution of 1.3 ml of TiCl4 in 7 ml of CCl4 is added dropwise. The reaction mixture is left stirring for 2 hours while the temperature is allowed to rise to r.t. It is poured into a mixture of concentrated HCl and ice, the resulting mixture is extracted with DCM, the organic phase is dried over magnesium sulphate and the solvents are evaporated off under vacuum. The residue is chromatographed on silica H, eluting with a DCM/heptane (70:30; v/v) mixture. 1.19 g of the expected product, m.p.=138° C., are obtained.

Workup

  1. waitThe reaction mixture is left
  2. customto rise to r.t
  3. extractionthe resulting mixture is extracted with DCM
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. customthe solvents are evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. washeluting with a DCM/heptane (70:30; v/v) mixture

Sources & evidence

ORD record
ord-7a6ed299f81c4a6fbce5980aab570c5e
Source dataset
uspto-grants-1997_08
Patent number
US05656648

Reaction notes

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