4,6-Dichloroguaiacol → HCID 21495080, compound

HRID 1731118Notes

Reaction equation

HRID 1731118 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[OH:11].[CH3:12]C[O-].[Na+].[Na].ClC[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>C(O)C>[O:24]1[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][CH2:10][O:9][C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=2[O:11][CH3:12])[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 280514,6-DichloroguaiacolHCID 958344-(3-Chloropropyl)morpholineHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 21495080HCID 21495080, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

54 g of 3,5-dichloroguaiacol (0.28 mole) is added to sodium ethylate produced by reacting 6.44 g of sodium on 84 ml of ethyl alcohol. 51 g (0.28 mole + 10% excess) of 1-chloro-3-morpholinopropane is added to the resulting solution. The mixture is heated under reflux for 8 hours. Precipitation of sodium chloride is observed. Cooling is effected and then the mixture is dissolved in 300 ml of water and 30 ml of concentrated hydrochloric acid. The resulting solution is filtered, then ammonia is added to precipitate the base which is extracted with ether. The ether is eliminated and the residue is distilled under vacuum.

Workup

  1. customproduced
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 8 hours
  4. customPrecipitation of sodium chloride
  5. temperatureCooling
  6. dissolutionthe mixture is dissolved in 300 ml of water
  7. filtrationThe resulting solution is filtered
  8. additionammonia is added
  9. customto precipitate the base which
  10. extractionis extracted with ether
  11. distillationthe residue is distilled under vacuum

Sources & evidence

ORD record
ord-1ae9b7a710e4427ba435779ae436bfde
Source dataset
uspto-grants-1976_11
Patent number
US03995037

Reaction notes

Loading…