Benzene → Allyl 11-mercaptoundecanoate

HRID 1081926

Reaktionsgleichung

Reaktionsgleichung von HRID 1081926
[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH2:15](O)[CH:16]=[CH2:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:17][CH:16]=[CH2:15])=[O:13]

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 7858Allyl AlcoholHCID 54350211-Mercaptoundecanoic Acid

Produkt 1

HCID 15834506Allyl 11-mercaptoundecanoateAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1.09 g (5 mmol) 11-mercaptoundecanoic acid was placed along with 3 g (51.7 mmol) allyl alcohol, 0.57 g p-toluenesulfonic acid and 40 ml benzene in a round bottom flask and heated for 25 minutes with azeotropic removal of water using a Dean-Stark apparatus. The reaction mixture was then cooled and washed with 10% aqueous sodium bicarbonate solution (3×20 ml). The benzene layer was dried over anhydrous MgSO4, and removal of solvent yielded a colorless oil (0.997 g, 77%). 1H-NMR (300 MHz, CDCl3) 1.27, m, 12 H; 1.60, m, 5 H; 2.33, t, 2 H, J=7.5 Hz; 2.51, q, 2 H, J=7.4 Hz; 4.59, dt, 2 H, J=5.7, 1.4 Hz; 5.20-5.39, m, 2 H; 5.85-6.00, m, 1 H; IR (film) 2560 (SH), 1730 (C=O), 1640 cm-1 (C=C); EI-MS; 258 (M+).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled
  2. washwashed with 10% aqueous sodium bicarbonate solution (3×20 ml)
  3. dry with materialThe benzene layer was dried over anhydrous MgSO4, and removal of solvent

Quellen und Nachweise

ORD-Eintrag
ord-1875606f79d846a7a10333953c7660ae
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587475

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