Reacción #1596974

Ecuación de reacción

Ethyl p-hydroxybenzoate

5-bromopentylvinyl ether

potassium carbonate

N,N-dimethylacetamide

→

4-(5-vinyloxypentyloxy)benzoic acid

Rendimiento 128.6%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooled
2. 2
   Extracciónextracted with ethyl acetate (500 mL)
3. 3
   Lavadowashed two times with water (100 mL)
4. 4
   SecadoThis was dried with anhydrous magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   OtroThe solvent was removed through concentration under reduced pressure
7. 7
   workup.DISSOLUTIONthe residue was dissolved in methanol (100 mL)
8. 8
   workup.ADDITIONgradually added
9. 9
   Temperaturaheated
10. 10
    Temperaturaunder reflux for 2 hours
11. 11
    TemperaturaAfter cooled
12. 12
    Filtraciónthe formed crystal was collected through filtration
13. 13
    workup.DISSOLUTIONdissolved in water (1 L)
14. 14
    workup.ADDITIONConcentrated hydrochloric acid (25.7 mL) was added
15. 15
    Filtraciónthe precipitated crystal was collected through filtration under reduced pressure
16. 16
    Lavadowashed with water
17. 17
    OtroThis was dried

Procedimiento

Ethyl p-hydroxybenzoate (33.2 g), 5-bromopentylvinyl ether (58.0 g), potassium carbonate (41.5 g) and N,N-dimethylacetamide (200 mL) were put into a 500-mL three-neck flask, and stirred at 120° C. for 5 hours. After cooled, the reaction mixture was poured into water (200 mL), extracted with ethyl acetate (500 mL), and washed two times with water (100 mL). This was dried with anhydrous magnesium sulfate, and filtered. The solvent was removed through concentration under reduced pressure, the residue was dissolved in methanol (100 mL), and a methanol solution (20 mL) of potassium hydroxide (16.8 g) was dropwise and gradually added thereto, and heated under reflux for 2 hours. After cooled, the formed crystal was collected through filtration and dissolved in water (1 L). Concentrated hydrochloric acid (25.7 mL) was added thereto, and the precipitated crystal was collected through filtration under reduced pressure, and washed with water. This was dried to give 4-(5-vinyloxypentyloxy)benzoic acid (TP-29C) (64.3 g, 90%). Production of 2,3,6,7,10,11-hexa(4-(5-vinyloxypentyloxy)benzoyloxy)triphenylene (TP-29):

Fuente