Acetic Acid → 2-Methylbenzoic acid

HRID 618998Notes

Reaction equation

HRID 618998 reaction equation
[O:1]=O.ON1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14].[C:15]([OH:18])(=[O:17])[CH3:16]>CC1C=CC=CC=1C>[C:8]([OH:1])(=[O:9])[C:7]1[C:16](=[CH:11][CH:12]=[CH:13][CH:6]=1)[C:15]([OH:18])=[O:17].[CH3:8][C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[C:5]([OH:14])=[O:17]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 977OxygenHCID 10665N-Hydroxyphthalimide

Product 2

HCID 1017Phthalic AcidYield 18%HCID 83732-Methylbenzoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
100 °C

Procedure

In an oxygen atmosphere, a mixture of 1.06 grams (10 millimoles) of o-xylene, 0.16 gram (1 millimole) of N-hydroxyphthalimide, 0.018 gram (0.05 millimole) of acetylacetonatocobalt(III) Co(AA)3 and 25 milliliters of acetic acid was stirred at a temperature of 100° C. for 6 hours. As a result, o-xylene was transformed into phthalic acid (yield 18%) and o-methylbenzoic acid (yield 71%) with a transformation rate of 92%.

Sources & evidence

ORD record
ord-d550842cab414df8a5ca99a59431720b
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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