Pyridine → HCID 131710345, compound

HRID 1658568Notes

Reaction equation

HRID 1658568 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8].[C:10]1(=[O:20])[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.N1C=CC=CC=1>CCOCC>[C:10]([OH:15])(=[O:20])[C:11]1[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:13]([OH:9])=[O:14].[CH:1]#[C:2][CH2:3][CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6811Phthalic AnhydrideHCID 1036561-Octyn-4-ol

Product 1

HCID 131710345HCID 131710345, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture consisting of 6.3 parts of 1-octyn-4(RS)-ol, 7.4 parts of phthalic anhydride and 10 parts by volume of pyridine is heated at the reflux temperature for about 3 hours, then allowed to cool for about 16 hours. At the end of that time the mixture is diluted with ether, then is washed with dilute hydrochloric acid. Extraction with dilute sodium hydroxide, followed by acidification of the alkaline extract affords an aqueous solution which is then extracted with ether. The ether extract is dried over anhydrous sodium sulfate, decolorized with activated carbon and stripped of solvent to afford 1-octyn-4(RS)-ol phthalate.

Workup

  1. temperatureis heated at the reflux temperature for about 3 hours
  2. temperatureto cool for about 16 hours
  3. washis washed with dilute hydrochloric acid
  4. extractionExtraction with dilute sodium hydroxide
  5. extractionextract
  6. customaffords an aqueous solution which
  7. extractionis then extracted with ether
  8. extractionThe ether extract
  9. dry with materialis dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-73f143343bde44b280b50688de21b43e
Source dataset
uspto-grants-1976_06
Patent number
US03965143

Reaction notes

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