Pyridine → HCID 54144848, compound

HRID 1576994Notes

Reaction equation

HRID 1576994 reaction equation
[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:18])[CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([CH3:16])[CH3:15])=[CH:3][C:4]([OH:6])=[O:5].N1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S(Cl)(Cl)=O.[CH2:29](OCC)C>>[C:20]1([O:5][C:4](=[O:6])[CH:3]=[C:2]([CH3:1])[CH2:7][CH2:8][CH:9]=[C:10]([CH3:18])[CH2:11][CH2:12][C:13]([CH3:17])=[C:14]([CH3:16])[CH3:15])[CH:29]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 54027525HCID 54027525, compound

Product 1

HCID 54144848HCID 54144848, compound

Procedure

To 10 g. of 3,7,10,11-tetramethyl-2,6,10-dodecatrienoic acid and 3.8 ml. of absolute pyridine in 80 ml. of absolute diethyl ether, 5.4 ml. of thionyl chloride were added dropwise under cooling. The reaction mixture was continually stirred for 75 minutes at 0°-2°C. Thereafter, the resulting mixture was filtered with precipitated pyridine hydrochloride and the filtrate was evaporated under vacuum. After evaporation, the residue was mixed into 20 ml. of absolute benzene. To this reaction mixture there was added dropwise 3.9 g. of phenol and 3.8 ml. of absolute pyridine in 170 ml. of absolute benzene. This addition was carried out dropwise. The resulting reaction mixture was continually stirred at room temperature for 2 hours. After this period, the reaction mixture was poured over dilute ice-cold hydrochloric acid and exhaustively extracted with benzene. The combined benzene extracts were diluted with an aqueous sodium bicarbonate solution. After this, the dilute extract is washed with a saturated sodium chloride solution and dried over sodium sulfate and evaporated. By chromatography on Kieselgel with hexane/diethyl ether (95:5 parts by volume) there is obtained pure 3,7,10,11-tetramethyl-2,6,10,-dodecatrienoic acid phenyl ester; b.p. 135°-140°C./0.001 mmHg (bulb tube distillation).

Workup

  1. temperatureunder cooling
  2. filtrationThereafter, the resulting mixture was filtered with precipitated pyridine hydrochloride
  3. customthe filtrate was evaporated under vacuum
  4. customAfter evaporation
  5. additionthe residue was mixed into 20 ml
  6. additionTo this reaction mixture there was added dropwise 3.9 g
  7. additionThis addition
  8. customThe resulting reaction mixture
  9. stirringwas continually stirred at room temperature for 2 hours
  10. waitAfter this period
  11. additionthe reaction mixture was poured over dilute ice-cold hydrochloric acid
  12. extractionexhaustively extracted with benzene
  13. additionThe combined benzene extracts were diluted with an aqueous sodium bicarbonate solution
  14. extractionAfter this, the dilute extract
  15. washis washed with a saturated sodium chloride solution
  16. dry with materialdried over sodium sulfate
  17. customevaporated

Sources & evidence

ORD record
ord-4efb401b523e46beada5fa8766754f6e
Source dataset
uspto-grants-1976_09
Patent number
US03983243

Reaction notes

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