Reaction #511473

Reaction equation

11-bromoundecanoic acid t-butyl ester

NaNO2

phloroglucinol

→

solid

Yield 42.0%

11-Nitroundecanoic acid tert-butyl ester

Yield 42.0%

Solvents

DMF

Conditions

Workup

1. 1
   OtherAfter separation
2. 2
   Extractionthe aqueous phase was further extracted with PET (3×30mL)
3. 3
   Dryingdried (Na2SO4)
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe crude product was purified by silica-gel column chromatography (PET/diethyl ether 95/5)

Procedure

In a 100 ml two-neck round bottom flask 11-bromoundecanoic acid t-butyl ester (6.10 g, 19.0 mmol) was dropped into a stirred solution of NaNO2 (2.60 g, 38.0 mmol) and phloroglucinol (3.10 g, 19.0 mmol) in DMF (10 ml). The reaction mixture was warmed at 50° C. and stirred for 24 h, then poured into a mixture of 40 mL of ice/water and 40 mL of PET. After separation, the aqueous phase was further extracted with PET (3×30mL), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by silica-gel column chromatography (PET/diethyl ether 95/5) obtaining a light yellow solid (2.29 g, 42%). M.p. 39-42° C. ESI-MS: 288 (MH+); (Calc. for C15H29NO4: 287 u.m.a.).

Source