Water → Dihydro-3-(2-nitrophenoxy)-2-(3H)-furanone

HRID 1267831Notes

Reaction equation

HRID 1267831 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20].O>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 10751552Dihydro-3-(2-nitrophenoxy)-2-(3H)-furanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-nitrophenol (20 g, 0.14 mol) and K2CO3 (25.2 g, 0.18 mol) in 280 mL DMF was cooled to 0 ° C. 2-Bromobutyrolactone was added dropwise, the reaction was stirred for 45 min at 0° C., then stirred at room temperature for 3 hours (h). The mixture was poured into 2 L water containing approx. 200 g salt, and the solution was washed with 6×100 mL of 1:1 diethyl ether/ethyl acetate. The combined organics were washed with 2×100 mL sat'd aq. K2CO3, 5×100 mL water and 100 mL brine, dried (Na2SO4), and filtered. Solvent was removed in vacuo to yield the title compound as an off-white solid (21.88 g, 0.1 mol). 1H (CDCl3): 7.84 (d, 1H, J=7.9), 7.57 (t, 1H, J=7.5), 7.49 (d, 1H, J=7.9), 7.16 (t, 1H, J=7.5), 5.03 (t, 1H, J=7.4), 4.58 (m, 1H), 4.42 (m, 1H), 2.8-2.6 (m, 2H).

Workup

  1. stirringstirred at room temperature for 3 hours (h)
  2. washthe solution was washed with 6×100 mL of 1:1 diethyl ether/ethyl acetate
  3. washThe combined organics were washed with 2×100 mL
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-31e74c5d0d9a4262baecd2b0b822dee3
Source dataset
uspto-grants-2003_04
Patent number
US06555536B2

Reaction notes

Loading…