Thionyl Chloride → 5-Chloro-2-methoxybenzoyl chloride

HRID 1028165Notes

Reaction equation

HRID 1028165 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. The white solid obtained 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. customThe white solid obtained
  9. customwas taken directly on to the next step without purification

Sources & evidence

ORD record
ord-90ec2b73a42d4926b2c4142ac59f7a9c
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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