Reaction #334986

Reaction equation

hydrochloric acid

2-fluoro-4-hydroxybenzoic acid

tridecanoyl chloride

dimethylaminopyridine

→

titled compound

Yield 59.4%

2-fluoro-4-n-tridecanoyloxybenzoic acid

Yield 59.4%

Solvents

dichloromethane

triethylamine

Conditions

Workup

1. 1
   OtherThe organic layer was separated by a funnel
2. 2
   workup.DISTILLATIONdistilled
3. 3
   Otherto remove the solvent
4. 4
   WashThe residue was washed with n-hexane
5. 5
   Otherdried

Procedure

To a solution of 2-fluoro-4-hydroxybenzoic acid (1.4 g) and triethylamine (1.0 g) in dichloromethane (40 ml) were added tridecanoyl chloride (2.0 g) and dimethylaminopyridine (0.2 g). The solution was stirred at room temperature for about 20 hours and thereto was added dilute aqueous hydrochloric acid solution. The organic layer was separated by a funnel and distilled to remove the solvent. The residue was washed with n-hexane and dried to obtain the titled compound (about 1.8 g).

Source