Ethoxyquin → HCID 20558605, compound

HRID 1659857Notes

Reaction equation

HRID 1659857 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[C:8]2[C:10]([CH3:16])=[CH:11][C:12]([CH3:15])([CH3:14])[NH:13][C:7]2=[CH:6][CH:5]=1.[C:17](Cl)([Cl:19])=[O:18]>C(OC(=O)C)C>[Cl:19][C:17]([N:13]1[C:7]2[C:8](=[CH:9][C:4]([O:3][CH2:2][CH3:1])=[CH:5][CH:6]=2)[C:10]([CH3:16])=[CH:11][C:12]1([CH3:15])[CH3:14])=[O:18]

Participants

4

Reactant 2

HCID 3293EthoxyquinHCID 6371Phosgene2×

Product 1

HCID 20558605HCID 20558605, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of ethoxyquin (30 g) in ethylacetate (300 ml) was added dropwise at room temperature to a stirred saturated solution of phosgene in ethylacetate (100 ml). Phosgene was rapidly and continuously bubbled into the stirred solution during the period of addition (2 hours). After the addition of the ethoxyquin solution was finished, phosgene bubbling was stopped and the solvent was gradually distilled (atmospheric pressure). At the end of the distillation, CCl4 (50 ml) was added and distillation continued under a slow stream of N2 (to eliminate traces of phosgene), another portion of CCl4 (50 ml) was added. Undesired ethoxyquin hydrochloride was filtered off (9.26 g), and the filtrate was evaporated to dryness under reduced pressure, yielding 1-Chlorocarbonyl-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline as yellow, viscous syrup, which crystallised on standing (31.67 g). Recrystallisation from acetone. m.p.: 75.5°-76.5°.

Workup

  1. customcontinuously bubbled into the stirred solution during the period of addition (2 hours)
  2. additionAfter the addition of the ethoxyquin solution
  3. distillationthe solvent was gradually distilled (atmospheric pressure)
  4. distillationAt the end of the distillation, CCl4 (50 ml)
  5. additionwas added
  6. distillationdistillation
  7. additionanother portion of CCl4 (50 ml) was added
  8. filtrationUndesired ethoxyquin hydrochloride was filtered off (9.26 g)
  9. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f2d1d32b9f764f3487de8012090c2aba
Source dataset
uspto-grants-1981_12
Patent number
US04305932

Reaction notes

Loading…