Aniline → HCID 15715944, compound

HRID 1448870Notes

Reaction equation

HRID 1448870 reaction equation
[CH3:1][C:2](=[CH:5][CH:6]([CH3:12])[CH2:7][C:8]([CH3:11])=[CH:9][CH3:10])[CH:3]=O.NC1C=CC=CC=1.S([O-])([O-])(=O)=[O:21].[Na+].[Na+].[OH-].[K+]>CCOCC>[CH3:12][CH:6]1[CH2:5][C:2]([CH3:3])([CH3:1])[C:9]([CH:10]=[O:21])=[C:8]([CH3:11])[CH2:7]1

Participants

6

Reactant 4

HCID 6115AnilineHCID 14797Potassium HydroxideHCID 24436Sodium SulfateHCID 544771132,4,6-Trimethyl-2,6-octadienal

Product 1

HCID 15715944HCID 15715944, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of the two isomeric aldehydes obtained according to paragraph (d) (36.5 g.), aniline (21.4 g.) and anhydrous sodium sulphate (20 g.) in 55 ml. of ether was left at 20° under stirring during one night. After having filtered washed and concentrated to the initial volume the solution was poured with vigorous stirring into 221 ml. of conc. H2SO4 and 22.1 g. of ice. The temperature was kept between -20 and -25° during 1 h., and the mixture was then added to 300 g. of ice and immediately distilled by means of steam distillation. The distillate was saturated with NaCl, extracted with ether and treated as usual. 36 g. of a mixture of crude α- and β-cyclocitral were thus obtained. The subsequent isomerisation was carried out at -10° in 120 ml. of a 8.5% Chanolic KOH solution (80% ethanol). The mixture was allowed to react during 3 h. in an atmosphere of argon, diluted then with pet.-ether (30°-50°), poured into 400 ml. of a NaCl saturated aqueous solution and finally extracted with pet.-ether. By distillation 4-methyl-β-cyclocitral was obtained:

Workup

  1. customobtained
  2. filtrationAfter having filtered
  3. washwashed
  4. concentrationconcentrated to the initial volume the solution
  5. additionwas poured
  6. stirringwith vigorous stirring into 221 ml
  7. additionthe mixture was then added to 300 g
  8. distillationof ice and immediately distilled by means of steam distillation
  9. extractionextracted with ether
  10. additiontreated as usual
  11. additionof a mixture of crude α- and β-cyclocitral
  12. customwere thus obtained
  13. customwas carried out at -10° in 120 ml
  14. customto react during 3 h. in an atmosphere of argon
  15. additiondiluted
  16. extractionof a NaCl saturated aqueous solution and finally extracted with pet
  17. distillationBy distillation 4-methyl-β-cyclocitral
  18. customwas obtained

Sources & evidence

ORD record
ord-b525e3dfb071411daf2341be82e9dc24
Source dataset
uspto-grants-1980_02
Patent number
US04187863

Reaction notes

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