Oxalyl chloride → HCID 20039095, compound

HRID 1904415Notes

Reaction equation

HRID 1904415 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[C:13](Cl)(=O)[C:14](Cl)=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:13][CH3:14])=[O:6]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 5971642-Methoxy-4-methylbenzoic acid

Product 1

HCID 20039095HCID 20039095, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 2-methoxy-4-methylbenzoic acid (35 g, 0.211 mol) in benzene (400 ml) was treated dropwise with oxalyl chloride (40 g, 0.317 mol). After 3 hours at room temperature the solvent and excess oxalyl chloride were evaporated under reduced pressure and the resulting crude acid chloride residue was treated with ethanol (200 ml) and heated under reflux for 1 hour. The solvent was evaporated off under reduced pressure to give the crude product which was purified by column chromatography (silica gel, dichloromethane) to yield ethyl 2-methoxy-4-methylbenzoate as a pale yellow oil having the following structural characteristics:

Workup

  1. customAfter 3 hours at room temperature the solvent and excess oxalyl chloride were evaporated under reduced pressure
  2. additionthe resulting crude acid chloride residue was treated with ethanol (200 ml)
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. customThe solvent was evaporated off under reduced pressure
  6. customto give the crude product which
  7. customwas purified by column chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-bbd6a2b404ed4ccf95fccfa41dc134f3
Source dataset
uspto-grants-1989_06
Patent number
US04837333

Reaction notes

Loading…