Hydrochloric Acid → HCID 4398594, compound

HRID 2257127Notes

Reaction equation

HRID 2257127 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1.Cl>C(Cl)(Cl)(Cl)Cl>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([O:24][CH3:25])[CH:21]=[CH:22][C:23]=1[C:9](=[O:10])[CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 90251,3-DimethoxybenzeneHCID 64801Benzenepropanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 4398594HCID 4398594, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 45.5 g of 3-phenylpropanoyl chloride in 50 ml of CCl4 is added dropwise to a suspension of 43.2 g of AlCl3 and 37.5 g of 1,3-dimethoxybenzene in 210 ml of CCl4. The reaction mixture is left stirring for 1 hour at r.t. and poured into a mixture of 400 g of ice and 150 ml of concentrated HCl. After 30 minutes of stirring, the resulting mixture is extracted with DCM, the combined organic phases are washed with saturated sodium hydrogen carbonate solution and dried over sodium sulphate and the solvents are evaporated off under vacuum. 66.5 g of oil of the expected product are obtained, which oil is used as it is.

Workup

  1. waitThe reaction mixture is left
  2. stirringAfter 30 minutes of stirring
  3. extractionthe resulting mixture is extracted with DCM
  4. washthe combined organic phases are washed with saturated sodium hydrogen carbonate solution
  5. dry with materialdried over sodium sulphate
  6. customthe solvents are evaporated off under vacuum

Sources & evidence

ORD record
ord-8a53b6f99ba84efd8ccffc6aacd81b77
Source dataset
uspto-grants-1997_08
Patent number
US05656648

Reaction notes

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