3-Nitrophenol → 4-(4-Nitrophenoxymethyl)-2-methoxycarbonyl-furan

HRID 76456

Reaction equation

HRID 76456 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].ClC[C:13]1[O:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:14]=1.[C:22]([O-])([O-])=[O:23].[K+].[K+]>CC(C)=O.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:23][CH2:22][C:14]2[CH:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[O:17][CH:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 75065Methyl 5-(chloromethyl)-2-furoate

Product 1

HCID 220610744-(4-Nitrophenoxymethyl)-2-methoxycarbonyl-furanYield 90.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3-Nitrophenol (1.0 g, 7.19 mmole), methyl 5-(chloromethyl)-2-furoate (1.38 g, 7.90 mmole) and anhydrous K2CO3 (1.19 g, 8.60 mmole) in acetone (30 mL) were refluxed for 8 h. The reaction mixture was cooled and diluted with water. The resultant white solid was filtered, washed with water and air dried overnight to give 1.81 g (90%) of the desired product. 1H NMR (CDCl3): δ 7.86 (dd, 1H, J=2.3 and 8.2 Hz), 7.80 (t, 1H, J=2.3 Hz), 7.45 (t, 1H, J=8.2 Hz), 7.27 (dd, 1H, J=2.3 and 8.2 Hz), 7.17 (d, 1H, J=3.5 Hz), 6.58 (d, 1H, J=3.5 Hz), 5.13 (s, 2H), 3.90 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationThe resultant white solid was filtered
  3. washwashed with water and air
  4. customdried overnight

Sources & evidence

ORD record
ord-1dded64bcf014bb381b1da1fe37c5cbb
Source dataset
uspto-grants-2014_09
Patent number
US08835430B2

Linked notes

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