3-Methylbenzoic acid → 3-Methylbenzoyl chloride

HRID 37185

Reaction equation

HRID 37185 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7](O)=[O:8])[CH:2]=1.C(Cl)(=O)C([Cl:14])=O>C1C=CC=CC=1.CN(C=O)C>[CH3:10][C:1]1[CH:2]=[C:3]([CH:4]=[CH:5][CH:6]=1)[C:7]([Cl:14])=[O:8]

Participants

5

Reactant 2

HCID 74183-Methylbenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 743753-Methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

Meanwhile, the 3-methylbenzoyl chloride acylating agent was prepared by suspending 3.016 g (22.0 mmol) of m-toluic acid in 100 ml benzene. To this solution was added 2.0 equiv. (3.84 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-327c30f17ea74844a93444c148790f2c
Source dataset
uspto-grants-1995_05
Patent number
US05420134

Linked notes

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