Hydrochloric Acid → HCID 58788081, compound

Temperature

80 °C

Methyl 3,5-dihydroxybenzoate (4.2 g, 25 mmol) was dissolved in 25 mL of dry DMF and then 13.86 g (100 mmol) of K2CO3 was added in the reaction mixture, where the above mixture was stirred at 80° C. for 1 h under a N2 atmosphere and then 1-bromododecane (12.4 g, 50 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at 90° C. for 24 h under N2. At the end of the reaction, the mixture was poured onto ice, 2N—HCl and extracted with MC, H20, NaHCO3 and brine. The solvent was removed in vacuo. The crude solid was purified by column chromatograph with 10% EA and hexane to yield 75% of the product. 1H-NMR (300 MHz, CDCl3) δ 7.1 (d, 2H), 6.6 (t, 1H), 4.0 (t, 4H), 3.9 (s, OCH3), 1.7-1.8 (m, 4H), 1.4-1.6 (m, 4H), 1.1-1.3 (m, 32H), 0.9 (t, 6H).

1. stirringThe reaction mixture was stirred at 90° C. for 24 h under N2
2. customAt the end of the reaction
3. extractionextracted with MC, H20, NaHCO3 and brine
4. customThe solvent was removed in vacuo
5. customThe crude solid was purified by column chromatograph with 10% EA and hexane

ORD record

ord-1503100fd0a140e4b6c166bd9dff28a2

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618298B2