Ethanol → HCID 178469588, compound

HRID 1787674Notes

Reaction equation

HRID 1787674 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.C([O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.C(O)C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH2:18]([O:17][C:15]([C:14]1[CH:20]=[N:7][C:6]2[C:8]([C:13]=1[OH:12])=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 6871Diethyl (ethoxymethylene)malonateHCID 7732P-Anisidine

Product 1

HCID 178469588HCID 178469588, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

A solution of 4-methoxyaniline (40 g, 0.32 mole) and diethyl ethoxymethylenemalonate (65 mL, 0.32 mole) in Dowtherm A (500 mL) was heated at reflux in a flask fitted with side-arm and condenser, and heating was continued until all the ethanol had distilled off (ca. 0.5 hr). The solution was cooled and pentane was added to give a sticky precipitate. The solvents were decanted off and the residue was treated with more pentane and allowed to stand overnight. The solid was filtered off and washed well with pentane to give the title compound (62.4 g; 78%, contains traces of Dowtherm A).

Workup

  1. temperatureat reflux in a flask
  2. customfitted with side-arm and condenser
  3. temperatureheating
  4. distillationhad distilled off (ca. 0.5 hr)
  5. temperatureThe solution was cooled
  6. additionpentane was added
  7. customto give a sticky precipitate
  8. customThe solvents were decanted off
  9. additionthe residue was treated with more pentane
  10. filtrationThe solid was filtered off
  11. washwashed well with pentane

Sources & evidence

ORD record
ord-5d28d319d39441ada334f0a675ea1006
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

Loading…