Hydrochloric Acid → HCID 19028024, compound

HRID 2257124Notes

Reaction equation

HRID 2257124 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:15])[CH2:13][CH3:14].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:15])[CH2:13][CH3:14])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 1389051-Chloro-2,4-dimethoxybenzene

Product 1

HCID 19028024HCID 19028024, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 5943Carbon TetrachlorideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2.01 g of 1-chloro-2,4-dimethoxybenzene and 1.08 g of propionyl 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 (80:20; v/v) mixture. 1.14 g of expected product, m.p.=115° 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 (80:20; v/v) mixture

Sources & evidence

ORD record
ord-994aeb9de98a4fbc9f82263155ff74b6
Source dataset
uspto-grants-1997_08
Patent number
US05656648

Reaction notes

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