Diethyl Ether → (3R,7R)-3,7,11-trimethyldodecyl p-toluenesulfonate

HRID 580371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 580371
[CH3:1][C@H:2]([CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:3][CH2:4][OH:5].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.CCOCC>N1C=CC=CC=1>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:5][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:6][CH2:7][CH2:8][C@H:9]([CH3:16])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 1590641-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-

Produkt 1

HCID 10317779(3R,7R)-3,7,11-trimethyldodecyl p-toluenesulfonateAusbeute 94,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 10.44 g (45.8 mmol) of (3R,7R)-3,7,11-trimethyldodecan-1-ol in 150 mL of anhydrous pyridine was stirred in an acetone-ice bath while 17.4 g (91.3 mmol) of p-toluenesulfonyl chloride was added in one portion. The mixture was stirred in the acetone-ice bath for 2 hr then kept at 0° C. for 40 hr before being quenched by the addition of 300 mL of ice-water. The product was isolated by extraction with 3×300 mL of ether. The ether extracts were combined, washed with 400 mL of cold 3N HCl and saturated brine, then dried (MgSO4), filtered and concentrated in vacuo. There was obtained 16.6 g (94.9%) of (3R,7R)-3,7,11-trimethyldodecyl p-toluenesulfonate.

Aufarbeitung

  1. additionwas added in one portion
  2. custombefore being quenched by the addition of 300 mL of ice-water
  3. customThe product was isolated by extraction with 3×300 mL of ether
  4. washwashed with 400 mL of cold 3N HCl and saturated brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-45e15b4db4544279b2942e1e96fe1c5c
Quelldatensatz
uspto-grants-1988_06
Patentnummer
US04752646

Notizen zur Reaktion

Wird geladen…