Reaction #1596974

Reaction equation

Ethyl p-hydroxybenzoate

5-bromopentylvinyl ether

potassium carbonate

N,N-dimethylacetamide

→

4-(5-vinyloxypentyloxy)benzoic acid

Yield 128.6%

Solvents

water

Conditions

Workup

1. 1
   TemperatureAfter cooled
2. 2
   Extractionextracted with ethyl acetate (500 mL)
3. 3
   Washwashed two times with water (100 mL)
4. 4
   DryingThis was dried with anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   OtherThe 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
   Temperatureheated
10. 10
    Temperatureunder reflux for 2 hours
11. 11
    TemperatureAfter cooled
12. 12
    Filtrationthe 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
    Filtrationthe precipitated crystal was collected through filtration under reduced pressure
16. 16
    Washwashed with water
17. 17
    OtherThis was dried

Procedure

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):

Source