Chemical Properties
Tan Solid
Uses
2-Methoxy-4''-hydroxyacetophenone (cas# 32136-81-5) is a compound useful in organic synthesis.
Preparation
Obtained by scission of 5-hydroxy-4-(4-hydroxyphenyl) 5H-furan-2-one with potassium hydroxide in methanol at 20° for 24 h (85%). – Also obtained by catalytic debenzylation of 1-(4-benzyloxyphenyl)-2-methoxyethanone in methanol under hydrogen (five bars) in the presence of 5% Pd/C for 24 h (81%).
Synthesis
General procedure for the synthesis of 1-(4-hydroxyphenyl)-2-methoxyacetophenone from 2-bromo-1-(4-hydroxyphenyl)acetophenone: Example 3 Preparation of α-methoxy-4-hydroxyacetophenone. Dissolve 2 g of α-bromo-4-hydroxyacetophenone in 11 g of methanol. 30g of methanol solution of saturated sodium hydroxide (1g NaOH dissolved in 4.2ml methanol) was slowly added dropwise to the above solution. Upon completion of the dropwise addition, the reaction mixture was poured into 30 g of ice water and the pH was adjusted with acid to 6. Subsequently, α-methoxy-4-hydroxyacetophenone precipitated as a precipitate, and after filtration and drying, a yellowish-green product was obtained in about 85% yield. The purity of the product was confirmed by 1H-NMR analysis.
References
[1] Patent: US5107034, 1992, A
