Oxalic Acid → M-Cresol

HRID 1647080Notes

Reaction equation

HRID 1647080 reaction equation
[CH2:1]([C:5]([CH3:7])=[O:6])[CH:2]([CH3:4])[CH3:3].[C:8]([OH:13])(=O)[C:9](O)=O>C(O)(=O)C>[CH:1]1[C:5]([OH:6])=[CH:7][CH:8]=[CH:3][C:2]=1[CH3:4].[CH:9]1[C:8]([OH:13])=[CH:5][CH:1]=[C:2]([CH3:4])[CH:3]=1

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 7909Methyl Isobutyl Ketone

Product 2

HCID 342M-CresolHCID 2879P-Cresol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 59.3 g of the polyphenol compound obtained in Referential Example 1, 133.2 g of m-cresol, 118.0 g of p-cresol, 250 g of methyl isobutyl ketone, 37.0 g of 11% aqueous solution of oxalic acid and 85 g of 90% acetic acid was dropwise added 135.9 g of 37% aqueous solution of formaldehyde with stirring at 95° C. over a period of one hour. After the addition, the resulting mixture was allowed to react at the same temperature as above for 15 hours. The reaction mixture was washed with water and dehydrated by azeotropic distillation to obtain a solution of a novolak resin in methyl isobutyl ketone. As measured by GPC, the novolak resin had a polystyrene-converted weight average molecular weight of 4,571.

Sources & evidence

ORD record
ord-bf308db81b51403f905e03d6da0cc7fc
Source dataset
uspto-grants-1995_07
Patent number
US05429904

Reaction notes

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