Dimethylformamide → Benzeneacetic acid, 4-(dodecyloxy)-

To a dimethylformamide (DMF, 100 ml) solution of ethyl 4-hydroxyphenyl acetate (18 g, 0.1 mol.) and dodecyl bromide (25 g, 0.1 mol.) was added potassium carbonate (15 g, 0.1 mol.). The mixture was stirred at 100° C. for one hour. To the reaction solution, after cooling, was added water (200 ml), which was subjected to extraction with isopropyl ether (IPE). The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was dissolved in a mixture of methanol (100 ml) and tetrahydrofuran (THF, 100 ml). To the solution was added aqueous sodium hydroxide (10 g, 0.25 xol.), and the mixture was stirred at 50° C. The reaction solution was concentrated under reduced pressure, and the pH was adjusted to 4, followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure to leave crude crystals Recrystallization from hexane-IPE gave 4-dodecyloxyphenylacetic acid (1-e, 20 g, 63%).

1. temperatureTo the reaction solution, after cooling
2. extractionwas subjected to extraction with isopropyl ether (IPE)
3. washThe organic layer was washed with water
4. customdried
5. concentrationconcentrated under reduced pressure
6. dissolutionThe concentrate was dissolved in a mixture of methanol (100 ml) and tetrahydrofuran (THF, 100 ml)
7. additionTo the solution was added aqueous sodium hydroxide (10 g, 0.25 xol.)
8. stirringthe mixture was stirred at 50° C
9. concentrationThe reaction solution was concentrated under reduced pressure
10. extractionfollowed by extraction with ethyl acetate
11. washThe organic layer was washed with water
12. customdried
13. concentrationconcentrated under reduced pressure
14. customto leave crude
15. customcrystals Recrystallization from hexane-IPE

ORD 기록

ord-558d21888ece4ddfa2b6bc46ff6f12ce

출처 데이터셋

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04939274