6-Hydroxy-2-methylchromone synthesis

5synthesis methods

Product Name:6-Hydroxy-2-methylchromone
CAS Number:22105-12-0
Molecular formula:C10H8O3
Molecular Weight:176.17

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22105-12-0
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Yield:22105-12-0 46%

Reaction Conditions:

Stage #1: 2,5-diacetoxyacetophenonewith potassium tert-butylate in tetrahydrofuran;
Stage #2: with sodium hydroxide;copper dichloride in tetrahydrofuran at 20; for 24 h;

Steps:

2.a Example 2: Synthesis of Compound of Formula (2) (2-Methyl-6-Chromanol) (see FIG. 3)

First step a): 1) KOtBu, tetrahydrofuran; 2) CuCl₂; 3) NaOH; 24 hours at room temperature; yield: 46%.Second step b): H₂, Pd/C; EtOH; 70° C., 7 days, 10 bar, yield: 20%.Starting from 2-acetyl-1,4-phenylene diacetate a base-mediated intramolecular aldol condensation furnishes the enone intermediate as described before (A. O. Termath, Stereoselektive Totalsynthese von a-Tocopherol durch Cu-katalysierte asymmetrische 1,4-Addition an ein Chromenon, Dissertation, Universit?t zu K?ln, ISBN 978-3-8439-1407-9, Verlag Dr. Hut, München, 2013; Chapter 6.2.2, page 196-197.). The subsequent hydrogenation, using similar conditions as for compound of formula (1) above, furnishes the product in 20% yield.

References:

US2021/30022,2021,A1 Location in patent:Paragraph 0174-0176