Thionyl Chloride → HCID 23436793, compound

HRID 2121087Notes

Reaction equation

HRID 2121087 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:6]1[CH:14]=[C:10]([C:11](O)=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1)=[O:5].S(Cl)([Cl:18])=O>>[CH3:1][O:2][CH2:3][C:4]([C:6]1[CH:14]=[C:10]([C:11]([Cl:18])=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1)=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 23436798HCID 23436798, compound

Product 1

HCID 23436793HCID 23436793, compoundYield 101.5%

Procedure

The above prepared 5-methoxyacetylsalicylic acid (26.24 g, 0.1250 mol) was placed in a 500 ml round bottomed flask fitted with Argon purge and magnetic stir bar. Methylene chloride (125 ml) and several drops of dimethylformamide were then added. A 60 ml addition funnel was placed atop the flask and thionyl chloride (22.30 g, 0.1874 mol) was added dropwise over a period of 25 minutes. The addition funnel was replaced with a condenser and the reaction mixture was heated at reflux for a period of approximately 1 hour. Heating was stopped and the reaction mixture allowed to cool to room temperature. Excess thionyl chloride and methylene chloride were removed under-vacuum yielding 29.00 g of 5-methoxyacetylsalicyloyl chloride.

Workup

  1. customwas placed in a 500 ml round bottomed flask
  2. customfitted with Argon
  3. custompurge
  4. additionMethylene chloride (125 ml) and several drops of dimethylformamide were then added
  5. additionA 60 ml addition funnel
  6. additionwas added dropwise over a period of 25 minutes
  7. customThe addition funnel was replaced with a condenser
  8. temperaturethe reaction mixture was heated
  9. temperatureat reflux for a period of approximately 1 hour
  10. temperatureHeating
  11. customExcess thionyl chloride and methylene chloride were removed under-vacuum

Sources & evidence

ORD record
ord-589777e8e54441179c1b0414ed377e4d
Source dataset
uspto-grants-2004_02
Patent number
US06693208B2

Reaction notes

Loading…