Reaktion #64033

Reaktionsgleichung

pyridine

(S)-3-(2-Hydroxyethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

thionyl chloride

→

(S)-3-(2-chloroethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

Ausbeute 61.3%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Waschenwashed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated

Vorschrift

(S)-3-(2-Hydroxyethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 -8.1° (C=0.62 in ethanol)) (70.5 g; 0.287 mol) was dissolved in toluene (700 g), and pyridine (25.0 g; 0.316 mol) was added thereto. The resulting mixture was cooled to 0° C., and thionyl chloride (41.0 g; 0.345 mol) was added dropwise thereto. After the addition was completed, the resultant mixture was heated at 60° C. for 5 hours. The reaction mixture was cooled, washed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order, dried over anhydrous sodium sulfate and concentrated to give (S)-3-(2-chloroethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (46.5 g; 0.176 mol; 61%). B.P., 106°-107° C./0.13 mmHg. [α]546 -33.4° (C=1.2 in ethanol).

Quelle