2-Methylbenzoic acid → 2-Methylbenzoyl chloride

HRID 37186

Reaction equation

HRID 37186 reaction equation
[C:1]1([CH3:10])[C:2]([C:7](O)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C(Cl)(=O)C([Cl:14])=O>C1C=CC=CC=1.CN(C=O)C>[CH3:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([Cl:14])=[O:8]

Participants

5

Reactant 2

HCID 83732-Methylbenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 702762-Methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

Meanwhile, the 2-methylbenzoyl chloride acylating agent was prepared by suspending 4.750 g (42.2 mmol) of o-toluic acid in 100 ml benzene. To this solution was added 2.0 equiv. (7.37 ml) of oxalyl chloride, dropwise via a pressure-equalizing dropping funnel at 0° 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. customat 0° C
  2. customthe ice bath was removed
  3. customThe solvent was removed by rotary vacuum evaporation
  4. customwas pumped down under high vacuum overnight

Sources & evidence

ORD record
ord-3f648e2bc73d4ea2a99c31b12348376b
Source dataset
uspto-grants-1995_05
Patent number
US05420134

Linked notes

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