Propionyl chloride → HCID 178458828, compound

HRID 235599Notes

Reaction equation

HRID 235599 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:5][C:4](=[O:18])[CH:3]=1.[C:19](Cl)(=[O:22])[CH2:20][CH3:21]>ClCCCl>[OH:18][C:4]1[CH2:5][CH:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:7][C:2](=[O:1])[C:3]=1[C:19](=[O:22])[CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 20193521HCID 20193521, compound

Product 1

HCID 178458828HCID 178458828, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Stannic chloride (12.0 g) was added dropwise to a mixture of 3-hydroxy-5-(naphth-1-yl)-cyclohex-2-en-1-one (10 g) and propionyl chloride (4.25 g) in 1,2-dichloroethane (50 ml). the mixture was stirred and heated at reflux under nitrogen for 6 hr. After cooling, the mixture was poured onto ice. The dichloromethane extract was evaporated and the residue was heated at reflux with a 2M sodium hydroxide solution (20 ml) for 2 hr. After cooling, the solution was poured into an ice/hydrochloric acid mixture. The dried (Na2SO4) dichloromethane extract was concentrated and the residue was purified by column chromatography over silica gel with dichloromethane elution to give 3-hydroxy-5-(naphth-1-yl)-2-propionylcyclohex-2-en-1-one as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 6 hr
  3. temperatureAfter cooling
  4. additionthe mixture was poured onto ice
  5. extractionThe dichloromethane extract
  6. customwas evaporated
  7. temperaturethe residue was heated
  8. temperatureat reflux with a 2M sodium hydroxide solution (20 ml) for 2 hr
  9. temperatureAfter cooling
  10. additionthe solution was poured into an ice/hydrochloric acid mixture
  11. dry with materialThe dried (Na2SO4) dichloromethane
  12. extractionextract
  13. concentrationwas concentrated
  14. customthe residue was purified by column chromatography over silica gel with dichloromethane elution

Sources & evidence

ORD record
ord-dc4f342fc65c4862bf62c5c471ce8b2b
Source dataset
uspto-grants-1987_02
Patent number
US04640708

Reaction notes

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