Thionyl Chloride → 5-Chloro-2-methoxybenzoyl chloride

HRID 2196793Notes

Reaction equation

HRID 2196793 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].O=S(Cl)[Cl:15]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([Cl:15])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 769705-Chloro-o-anisic acid

Product 1

HCID 123841765-Chloro-2-methoxybenzoyl chloride

Procedure

A solution of 5-chloro-2-methoxybenzoic acid (0.37 g, 2.0 mmol) in 10 mL of SOCl2 was warmed to reflux and was allowed to stir for 2 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The crude material was diluted with 5 mL of toluene and concentrated under reduced pressure. This dilution with toluene and concentration was repeated two additional times to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 3.82 (s, 3 H), 7.16 (d, J=8.8 Hz, 1 H), 7.49-7.59 (m, 1 H), 7.61 (d, J=2.7 Hz, 1 H).

Workup

  1. temperatureto reflux
  2. concentrationconcentrated under reduced pressure
  3. additionThe crude material was diluted with 5 mL of toluene
  4. concentrationconcentrated under reduced pressure
  5. concentrationThis dilution with toluene and concentration

Sources & evidence

ORD record
ord-2d760c3092034ae7a318a4895b5deeff
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

Loading…