Acetic Acid → 2-Methylbenzoic acid

HRID 618997Notes

Reaction equation

HRID 618997 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].ON1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[O:17]=O>CC1C=CC=CC=1C>[C:10]([OH:17])(=[O:11])[C:9]1[C:2](=[CH:13][CH:14]=[CH:15][CH:8]=1)[C:1]([OH:4])=[O:3].[CH3:10][C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[C:7]([OH:16])=[O:3].[C:10]1(=[O:11])[O:4][C:1](=[O:3])[C:2]2=[CH:13][CH:14]=[CH:15][CH:8]=[C:9]12

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 977OxygenHCID 10665N-Hydroxyphthalimide

Product 3

HCID 1017Phthalic AcidYield 40%HCID 6811Phthalic AnhydrideYield 10%HCID 83732-Methylbenzoic acidYield 46%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To 25 milliliters of acetic acid were added 1.06 grams (10 millimoles) of o-xylene, 0.16 gram (1 millimole) of N-hydroxyphthalimide and 0.018 gram (0.05 millimole) of acetylacetonatocobalt(II) Co(AA)2, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 100° C. for 6 hours. With a transformation rate of 98%, o-xylene was transformed into phthalic acid (yield 40%), o-methylbenzoic acid (yield 46%) and phthalic anhydride (yield 10%).

Sources & evidence

ORD record
ord-76af2f4e2daa45b8b8837d62a513061f
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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