Acetic Acid → 3,5-Dimethylbenzoic acid

HRID 1602067Notes

Reaction equation

HRID 1602067 reaction equation
[C:1]1([CH3:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[OH:10]N1C(=O)C2=CC=CC=C2C1=O.[C:22]([OH:25])(=[O:24])[CH3:23]>>[CH3:9][C:1]1[CH:6]=[C:5]([CH:4]=[C:3]([CH3:8])[CH:2]=1)[CH:7]=[O:10].[CH3:9][C:1]1[CH:6]=[C:23]([CH:4]=[C:3]([CH3:8])[CH:2]=1)[C:22]([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7947Mesitylene2×HCID 10665N-Hydroxyphthalimide

Product 2

HCID 103563,5-Dimethylbenzoic acidYield 71%HCID 34225Benzaldehyde, 3,5-dimethyl-Yield 14%

Procedure

To 25 ml of acetic acid were added 10 mmol of mesitylene, 1 mmol of N-hydroxyphthalimide and a binary co-catalyst [0.04 mmol of acetylacetonatocobalt Co(AA)2 and 0.005 mmol of acetylacetonatomanganese Mn(AA)2 ] and the resultant mixture was stirred under an oxygen atmosphere at a temperature of 70° C. for 3 hours. The products in the reaction mixture were analyzed by gas chromatography, and, as a result, mesitylene was converted into 3,5-dimethylbenzaldehyde (yield 14%) and 3,5-dimethylbenzoic acid (yield 71%) with a conversion of 91%.

Sources & evidence

ORD record
ord-bed8fc563f8f4a4b9a6104f51d8956cf
Source dataset
uspto-grants-1999_11
Patent number
US05981420

Reaction notes

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