Thionyl Chloride → 5-Chloro-2-methoxybenzoyl chloride

HRID 1888617Notes

Reaction equation

HRID 1888617 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]>C1(C)C=CC=CC=1>[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

4

Reactant 2

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

Product 1

HCID 123841765-Chloro-2-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Chloro-2-methoxybenzoic acid (11.3 g, 60.56 mmol) and SOCl2 (9 mL, 123.7 mmol) in toluene (20 mL) were heated gently while vigorous gas evolution occurred. After gas evolution had subsided, the reaction was heated to reflux for 1.5 h, cooled and stirred overnight at room temperature. The volatiles were evaporated in vacuo and the remaining material was treated with toluene and evaporated (2×) to remove excess SOCl2 to provide a white solid that was taken directly on to the next step without purification. 1H NMR (300 MHz, CDCl3) δ 3.92 (s, 3H), 6.95 (d, 1H), 7.53 (dd, 1H), 8.03 (d, 1H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1.5 h
  3. temperaturecooled
  4. customThe volatiles were evaporated in vacuo
  5. additionthe remaining material was treated with toluene
  6. customevaporated (2×)
  7. customto remove excess SOCl2
  8. customto provide a white solid that
  9. customwas taken directly on to the next step without purification

Sources & evidence

ORD record
ord-25431e28e435412cb743f147e937a566
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

Loading…