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ChemicalBook CAS DataBase List 2',4'-Dihydroxy-3'-methoxyacetophenone

2',4'-Dihydroxy-3'-methoxyacetophenone synthesis

3synthesis methods
Preparation by catalytic hydrogenolysis of 4-(benzyloxy)-2-hydroxy-3-methoxyacetophenone in the presence of 5% Pd/C in ethyl acetate (90%).
-

Yield:62615-26-3 32.2%

Reaction Conditions:

at 100; for 3 h;

Steps:

1-(2,4-dihydroxy-3-methoxyphenyl)ethan-1-one (3.2)

The solution of 2-methoxybenzene-1,3-diol (3.1) (0.501 g, 1.00 Eq, 3.57 mmol) in boron trifluoride - acetic acid complex (ca.33% BF3, 3.36 g, 2.48 mL, 5.00 Eq, 17.9 mmol) was heated to 100 °C for 180 min. The mixture was then poured into water and extracted with 20 mL DCM (3x) (Note: a leak occurred during the workup, so part of the product was lost and the yield cannot be final). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. Resulting product 1-(2,4-dihydroxy-3-methoxyphenyl)ethan-1-one (3.2) (0.210 g, 1.15 mmol, 32.2 %) was collected as dark yellow crystals.

References:

WO2021/53205,2021,A1 Location in patent:Page/Page column 64