Hydrochloric Acid → HCID 19028014, compound

HRID 2257126Notes

Reaction equation

HRID 2257126 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[CH3:19].Cl>C(Cl)Cl>[Cl:10][C:11]1[C:12]([CH3:19])=[CH:13][C:14]([O:17][CH3:18])=[C:15]([C:5](=[O:8])[CH2:6][CH3:7])[CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 4581561-Chloro-4-methoxy-2-methylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19028014HCID 19028014, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of 2.55 g of AlCl3 in 30 ml of DCM is cooled to 0° C. under a nitrogen atmosphere, and a solution of 1.77 g of propionyl chloride in 15 ml of DCM is added dropwise. A solution of 3 g of 2-chloro-5-methoxytoluene in 15 ml of DCM is then added dropwise, and the reaction mixture is left stirring for 2 hours. It is poured into a mixture of concentrated HCl and ice, the organic phase is extracted with DCM and dried over magnesium sulphate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica, eluting with a DCM/heptane (70:30; v/v) mixture. 2.2 g of the expected product, m.p.=79° C., are obtained.

Workup

  1. waitthe reaction mixture is left
  2. extractionthe organic phase is extracted with DCM
  3. dry with materialdried over magnesium sulphate
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica
  6. washeluting with a DCM/heptane (70:30; v/v) mixture

Sources & evidence

ORD record
ord-a9b53fc69a0145a78c11fdb9827c14e7
Source dataset
uspto-grants-1997_08
Patent number
US05656648

Reaction notes

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