Ethanol → Ethyl 3-nitro-1-naphthoate

HRID 1696482Notes

Reaction equation

HRID 1696482 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].O=S(Cl)Cl.[CH3:21][CH2:22]O>>[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O:16][CH2:21][CH3:22])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2307723-Nitro-1-naphthoic acid

Product 1

HCID 22262323Ethyl 3-nitro-1-naphthoate

Procedure

To a solution of 3-nitronaphthalene-1-carboxylic acid (4.34 g, 20 mmol) in EtOH (50 mL) was added SOCl2 (3.70 mL, 30 mmol) at 0° C. The mixture was heated at reflux for 2 h and then concentrated. The residue was recrystallized from EtOH to yield ethyl 3-nitronaphthalene-1-carboxylate (4.2 g). 1H NMR (300 MHz, DMSO-d6): δ 9.16 (s, 1H), 8.77 (d, J=8.7 Hz, 1H), 8.62 (s, 1H), 8.34 (d, J=8.1 Hz, 1H), 7.87 (t, J=7.2 Hz, 1H), 7.75 (t, J=7.2 Hz, 1H), 4.43 (q, J=7.2 Hz, 2H), 1.38 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationconcentrated
  4. customThe residue was recrystallized from EtOH

Sources & evidence

ORD record
ord-21d51a0db3434959be02f22173f077fb
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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