Dimethylformamide → 3-Formyl-5-methylbenzoic chloride

HRID 1656482Notes

Reaction equation

HRID 1656482 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:6](O)=[O:7])=[O:2].S(Cl)([Cl:15])=O.CN(C)C=O>C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[C:6]([Cl:15])=[O:7])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 197881733-Formyl-5-methylbenzoic acid

Product 1

HCID 197881563-Formyl-5-methylbenzoic chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 3-formyl-5-methylbenzoic acid (75.0 g, 0.457 moles), thionyl chloride (65 g, 0.0547 moles), and dimethylformamide (1 ml), in toluene (500 ml) was slowly warmed to 70° C. and stirred at that temperature for 2 h. The toluene was eliminated in a rotavap to yield 3-formyl-5-methylbenzoic chloride used in the next step as such.

Sources & evidence

ORD record
ord-6d3c04233a8e4a55bde39445076d3e8c
Source dataset
uspto-grants-1993_10
Patent number
US05254584

Reaction notes

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