Benzoic Acid → 4-Isopropylbenzoyl chloride

HRID 1973404Notes

Reaction equation

HRID 1973404 reaction equation
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(O)(=O)C1C=CC=CC=1.[Mn]([O-])(=O)(=O)=O.[K+].S(Cl)([Cl:29])=O>S(=O)(=O)(O)O.CN(C)C=O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([Cl:29])=[O:9])=[CH:10][CH:11]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 326CuminaldehydeHCID 24386Thionyl ChlorideHCID 516875Potassium Permanganate

Product 1

HCID 27594864-Isopropylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1118Sulfuric AcidSolvent

Procedure

p-isopropylbenzaldehyde is oxidized to the corresponding benzoic acid by using potassium permanganate in sulfuric acid as the oxidizing agent at low temperature. The acid is converted to the acid chloride using thionyl chloride with a trace of dimethylformamide as a catalyst to give p-isopropylbenzoyl chloride.

Sources & evidence

ORD record
ord-62f40fb078594978a10936064201b5ba
Source dataset
uspto-grants-1976_12
Patent number
US03997539

Reaction notes

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