P-Anisidine → HCID 291021, compound

HRID 371230Notes

Reaction equation

HRID 371230 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.S([O-])([O-])(=O)=O.[Mg+2].[CH:16](=O)/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[C:19]1([CH:18]=[CH:17][CH:16]=[N:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 637511Cinnamaldehyde

Product 1

HCID 291021HCID 291021, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Anisidine (12.32 g) is dissolved in 160 ml of methylene chloride and 20 g of anhydrous magnesium sulfate is added. The mixture is cooled in an ice bath and 13.22 g of transcinnamaldehyde is added. The mixture is stirred under nitrogen for 2 hours and then filtered. The filtrate is evaporated to give a solid. The crude product is recrystallized from methylene chloride-petroleum ether to give 20.96 g of the title compound as a solid.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. filtrationfiltered
  3. customThe filtrate is evaporated
  4. customto give a solid
  5. customThe crude product is recrystallized from methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-064d405af8644d4eba2e2c1bc9429629
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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