p-Anisoyl chloride → HCID 14460994, compound

HRID 893413Notes

Reaction equation

HRID 893413 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[CH3:16][O:17][C:18]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:19]=1[CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>ClCCCl>[CH3:16][O:17][C:18]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([C:11](=[O:12])[C:10]2[CH:14]=[CH:15][C:7]([O:6][CH3:5])=[CH:8][CH:9]=2)=[CH:27][C:19]=1[CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14521157HCID 14521157, compound

Product 1

HCID 14460994HCID 14460994, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

52 g of aluminum trichloride are suspended in 200 ml of 1,2-dichloroethane and cooled to 0° C. Then, at this temperature, 66.5 g of 4-methoxybenzoyl chloride are added dropwise, followed by 94.7 g of ethyl 2,4-dimethoxyhydrocinnamate in 30 ml of 1,2-dichloroethane. The mixture is then heated at 50° C. with exclusion of moisture until the reaction is complete. The reaction mixture is then poured onto ice-water, and the organic phase is separated off, diluted with 200 ml of methylene chloride and then extracted with sodium bicarbonate solution and water. It is dried over magnesium sulfate and concentrated. A gray-brown solid remains and is immediately reacted further.

Workup

  1. temperatureThe mixture is then heated at 50° C. with exclusion of moisture until the reaction
  2. additionThe reaction mixture is then poured onto ice-water
  3. customthe organic phase is separated off
  4. additiondiluted with 200 ml of methylene chloride
  5. extractionextracted with sodium bicarbonate solution and water
  6. dry with materialIt is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customA gray-brown solid remains and is immediately reacted further

Sources & evidence

ORD record
ord-a9f3fda88386443b83eed92905f661ae
Source dataset
uspto-grants-1992_06
Patent number
US05124478

Reaction notes

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