Thionyl Chloride → 3,3,3-Triphenylpropan-1-ol

HRID 443054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 443054
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O>C(O)C>[C:18]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:8][CH2:9][OH:10])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 1366963,3,3-Triphenylpropionic Acid

Produkt 1

HCID 2986573,3,3-Triphenylpropan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To an ethanol solution (300 ml) of 3,3,3-triphenylpropionic acid (15 g) was added dropwise, under ice-cooling, thionyl chloride (5 ml). The mixture was refluxed for 12 hours. The reaction mixture was cooled and concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate, which was washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution. The organic layer was dried, which was then concentrated under reduced pressure. The concentrate was dissolved in ether (50 ml), which was added dropwise, under ice-cooling, to an ether suspension (250 ml) of lithium aluminum hydride (1.89 g). The mixture was stirred for one hour at room temperature, which was processed with 10% HCl, followed by addition of ether. The organic layer was washed with water, dried and concentrated under reduced pressure (14.2 g).

Aufarbeitung

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 12 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe concentrate was dissolved in ethyl acetate
  6. washwhich was washed with water
  7. customThe organic layer was dried
  8. concentrationwhich was then concentrated under reduced pressure
  9. dissolutionThe concentrate was dissolved in ether (50 ml)
  10. additionwhich was added dropwise, under ice-
  11. temperaturecooling, to an ether suspension (250 ml) of lithium aluminum hydride (1.89 g)
  12. additionfollowed by addition of ether
  13. washThe organic layer was washed with water
  14. customdried
  15. concentrationconcentrated under reduced pressure (14.2 g)

Quellen und Nachweise

ORD-Eintrag
ord-8dfd0e5201384be2be8a6f0e589c3439
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891916

Notizen zur Reaktion

Wird geladen…