P-Toluic Acid → 4-Methylbenzoyl Chloride

HRID 37184Notes

Reaction equation

HRID 37184 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[CH:6][CH:7]=1.C(Cl)(=O)C([Cl:14])=O>C1C=CC=CC=1.CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([Cl:14])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7470P-Toluic AcidHCID 65578Oxalyl chloride

Product 1

HCID 134054-Methylbenzoyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

Meanwhile, the 4-methylbenzoyl chloride acylating agent was prepared by suspending 3.314 g (24.3 mmol) of ρ-toluic acid in 200 ml benzene. To this solution was added 2.0 equiv. (4.25 ml) of oxalyl chloride, dropwise via a pressure-equalizing dropping funnel at O° C. DMF (2-3 drops) was added to the reaction mixture catalytically and the ice bath was removed. The progress of the reaction was monitored via infrared spectroscopy. The solvent was removed by rotary vacuum evaporation and the residual oil was pumped down under high vacuum overnight.

Workup

  1. customthe ice bath was removed
  2. customThe solvent was removed by rotary vacuum evaporation
  3. customwas pumped down under high vacuum overnight

Sources & evidence

ORD record
ord-2e7de4a67f654e6289e33cb572b49a01
Source dataset
uspto-grants-1995_05
Patent number
US05420134

Reaction notes

Loading…