Reaction #4815

Reaction equation

chloromethyl n-dodecanoate

1-methylimidazole

KBr

→

1-n-Dodecanoyloxymethyl-3-Methylimidazolium Chloride

Solvents

ether

Conditions

Workup

1. 1
   workup.ADDITIONwere mixed
2. 2
   Temperatureheated together at 90° for 3 hrs
3. 3
   Otherthe mixture was triturated in anhydrous ether overnite
4. 4
   OtherThe solid was isolated by filtration under a nitrogen atmosphere
5. 5
   Washthoroughly washed with anhydrous ether
6. 6
   DryingAfter drying in vacuo over calcium sulfate at room temperature
7. 7
   Other2.4 g (0.007 mol), 70%, 10 was obtained as a white solid, mp 60°-63°

Procedure

A mixture of 2.49 g (0.01 mol) chloromethyl n-dodecanoate and 0.82 g (0.01 mol) 1-methylimidazole were mixed and heated together at 90° for 3 hrs. On cooling to room temperature, anhydrous ether was added to the mixture and the mixture was triturated in anhydrous ether overnite. The solid was isolated by filtration under a nitrogen atmosphere and thoroughly washed with anhydrous ether. After drying in vacuo over calcium sulfate at room temperature, 2.4 g (0.007 mol), 70%, 10 was obtained as a white solid, mp 60°-63°; ir (KBr) 3400, 3110, 2960, 2920, 1750, 1470, 1140 and 770 cm-1 ; pmr (CDCl3) δ 10.8 (s, 1H), 8.0 (d, 2H), 6.4 (s, 2H), 4.2 (s, 3H), 2.4 (t, 2H), 1.4 (bs, 18H) and 0.9 (bt, 3H) ppm.

Source