Thionyl Chloride → 3-methoxy-4-nitro-benzoyl Chloride

HRID 891040Notes

Reaction equation

HRID 891040 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](O)=[O:7].S(Cl)([Cl:17])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6]([Cl:17])=[O:7]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 787643-Methoxy-4-nitrobenzoic acid

Product 1

HCID 111276553-methoxy-4-nitro-benzoyl ChlorideYield 87.3%

Procedure

A mixture of 3-methoxy-4-nitrobenzoic acid (2.01 g, 10.2 mmol) and thionyl chloride (2.3 mL, 31.5 mmol) was stirred at 80–90° C. for 1.5 h. The reaction was concentrated and the residue diluted with ether. The organic solution was washed with sat. aq. NaHCO3 (2×), H2O, then sat. aq. NaCl, dried (MgSO4) and concentrated to afford 3-methoxy-4-nitrobenzoyl chloride (1.92 g, 87%) as a white solid: 1H NMR (CDCl3, 300 MHz, ppm) 7.95–7.70 (m, 3H), 4.06 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue diluted with ether
  3. washThe organic solution was washed with sat. aq. NaHCO3 (2×), H2O
  4. dry with materialsat. aq. NaCl, dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34a693b8a0784200a499c3da52c13f7f
Source dataset
uspto-grants-2006_02
Patent number
US07001921B1

Reaction notes

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