Reaction #1483100

Reaction equation

2-bromo propionyl bromide

1-decanol

1-dodecanol

triethylamine

→

59

Yield 94.0%

dodecyl 2-bromopropanoate

Yield 94.0%

Solvents

toluene

Conditions

Workup

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

Procedure

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