1H-Indol-2-ol → (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid

Participants

Reaction Steps

The hydroxyindole compound was readily prepared by a literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl–3-H-indol–5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels, Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279–284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmol, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gave (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue.

Provenance & Evidence