Reaction #5259

Reaction equation

potassium hydroxide

10-iododecyl allyl ether

methyl p-hydroxybenzoate

potassium carbonate

hydrochloric acid

→

4-(10-allyloxydecyloxy)benzoic acid

Yield 80.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherAfter conclusion of the reaction
2. 2
   Otherthe acidified reaction solution
3. 3
   Concentrationwas then concentrated under reduced pressure
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   Otherto form a suspension
6. 6
   Otherthe insoluble matter was collected
7. 7
   Otherwas then dried

Procedure

70 mmol (22.7 g) of 10-iododecyl allyl ether, 70 mmol (10.6 g) of methyl p-hydroxybenzoate, and 70 mmol (9.6 g) of potassium carbonate were refluxed in absolute ethanol for 15 hours. After addition of an aqueous potassium hydroxide solution (containing 4.0 g of potassium hydroxide) into the reaction solution, the resulting mixture was further heated at 80° C. for 5 hours. After conclusion of the reaction, the reaction solution was acidified with hydrochloric acid, and the acidified reaction solution was then concentrated under reduced pressure. Water was added to the residue to form a suspension, and the insoluble matter was collected and was then dried, to obtain 18.7 g of 4-(10-allyloxydecyloxy)benzoic acid (Yield: 80%).

Source