Réaction #1483100

Équation de réaction

2-bromo propionyl bromide

1-decanol

1-dodecanol

triethylamine

→

59

Rendement 94.0%

dodecyl 2-bromopropanoate

Rendement 94.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was quenched with saturated sodium bicarbonate solution
2. 2
   workup.STIRRINGstirred for 15 minutes at 25-35° C
3. 3
   AutreThe aqueous and organic layers were separated
4. 4
   Lavagethe organic layer was washed with brine
5. 5
   Lavagethe combined organic layers were washed with brine solution
6. 6
   SéchageThe organic layer was dried over Na2SO4
7. 7
   Concentrationconcentrated under vacuum

Mode opératoire

To a stirred solution of 1-decanol 2 (10 g, 53.7 mmol) in toluene (100 mL) was added triethylamine (7.5 mL, 53.7 mmol)), followed by 2-bromo propionyl bromide 58 (12.7 g, 59.1 mmol) at 5-10° C. The reaction mixture was stirred for 3 hour at 55-60° C. and the reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium bicarbonate solution and stirred for 15 minutes at 25-35° C. The aqueous and organic layers were separated, the organic layer was washed with brine, and the combined organic layers were washed with brine solution. The organic layer was dried over Na2SO4 and concentrated under vacuum to afford crude 59 (16.2 g, yield: 94%) as a liquid.

Source