Reaction #1442485

ord-b5f58b4a9ac14795aaca94379e302bf9

Reaction equation

OB(O)O
Boric acid
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
sorbitol
NC(=O)c1ccccc1O
salicylamide
→
NC(=O)c1ccccc1O.OB(O)O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
salicylamide sorbitol borate
Yield 86.6%

Reactants

OB(O)O
Boric acid
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
sorbitol
NC(=O)c1ccccc1O
salicylamide

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherSalicylamide/sorbitol borate was prepared
  2. 2
    Otherthe byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation
  3. 3
    OtherThe final solution was evaporated
  4. 4
    Otherto remove toluene under vacuum

Procedure

Salicylamide/sorbitol borate was prepared as follows. Boric acid (10.3 grams), sorbitol (30.4 grams), and salicylamide (22.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a yellowish resinous product (˜55 grams) of salicylamide/sorbitol borate was obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06585816B1uspto-grants-2003_07