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

HRID 381248Notes

Reaction equation

HRID 381248 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%

Conditions

Temperature
85 °C

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-c7748e7282d14f21801d52087d00f045
Source dataset
uspto-grants-2001_10
Patent number
US06306840B1

Reaction notes

Loading…