Sulfuric Acid → 11-Mercaptoundecanoic Acid

4 g (15.09 mmol) 11-bromoundecanoic acid is added along with 1.505 g thiourea (19.82 mmol) and 15 ml water to a round botton flask, and the mixture is refluxed for 3 hours. 10.2 ml 3M sodium hydroxide (30.6 mmol) was then added and the mixture was refluxed for one additional hour. The reaction mixture was cooled in an ice bath, and dilute sulfuric acid was added dropwise until the solution had a pH of about 2. The cloudy solution was then extracted with ether (2×25 ml), dried over anhydrous MgSO4, and concentrated under reduced pressure to give a white solid (3.1 g, 94%). 1H-NMR (300 MHz, CDCl3) 1.28, m, 10 H; 1.60, m, 7 H; 2.35, t, 2 H, J=7.3 Hz; 2.50, q, 2 H, J =7.5 Hz.

1. temperaturethe mixture is refluxed for 3 hours
2. temperaturethe mixture was refluxed for one additional hour
3. temperatureThe reaction mixture was cooled in an ice bath
4. extractionThe cloudy solution was then extracted with ether (2×25 ml)
5. dry with materialdried over anhydrous MgSO4
6. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-49448244f37547c19b69413a688f40b3

Quelldatensatz

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05587475