Glyoxylic Acid → 3',4'-Methylenedioxymandelic acid

HRID 1449325Notes

Reaction equation

HRID 1449325 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].C(O)(=O)C=O.[CH2:12]1[O:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13]1>C1(C)C=CC=CC=1>[CH2:12]1[O:20][C:15]2[CH:16]=[CH:17][C:18]([CH:3]([OH:4])[C:2]([OH:6])=[O:5])=[CH:19][C:14]=2[O:13]1

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 92291,3-BenzodioxoleHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 1196183',4'-Methylenedioxymandelic acidYield 76.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

If, instead of glyoxylic acid monohydrate, an equivalent amount of 50% strength aqueous glyoxylic acid is employed and the mixture is stirred for 6 hours instead of 3.5 hours, 8.58 g of bis-3,4-methylenedioxyphenylacetic acid are obtained from the toluene phase and 73.4 g of 3,4-methylenedioxymandelic acid, corresponding to a yield of 76.3% of theory, relative to 1,2-methylenedioxybenzene employed, are obtained from the aqueous phase.

Sources & evidence

ORD record
ord-c58b4df85746410a9c26a7c32154be10
Source dataset
uspto-grants-1980_02
Patent number
US04190583

Reaction notes

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