Réaction #1960523

Équation de réaction

2-hydroxy-benzoic acid carboxymethyl ester

triethylamine

water

→

Aspirin

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dichloro linker (10 grams)
2. 2
   Températurerefluxed for 18 hours
3. 3
   Extractionwas extracted into ethyl acetate
4. 4
   LavageIt was washed with 5% sodium bicarbonate solution and water
5. 5
   Séchageby drying over sodium sulphate
6. 6
   workup.DISTILLATIONThe solvent was distilled off
7. 7
   Autreprecipitated with diisopropyl alcohol

Mode opératoire

To a mixture of 2-hydroxy-benzoic acid carboxymethyl ester (22.8 grams) and triethylamine (22.6 ml) in acetone (200 ml) was added dichloro linker (10 grams). The reaction mixture was stirred at room temperature for 1 hour and then refluxed for 18 hours. The reaction mixture was poured onto cold water and crude product was extracted into ethyl acetate. It was washed with 5% sodium bicarbonate solution and water, followed by drying over sodium sulphate. The solvent was distilled off and precipitated with diisopropyl alcohol to give 8 grams of pure Aspirin dimer diol as a white powder with a melting point of 99-102° C. The product was characterized by 1H NMR (DMSO-d6) δ 4.40 (s, 2H, CH2), 4.90 (s, 2H, CH2), 5.15 (s, 2H, CH2), 7.05 (m, 2H, Ar), 7.62 (t, 1H, Ar), 7.90 (d, 1H, Ar), 10.30 (s, 1H, ArOH).

Source