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ChemicalBook CAS DataBase List 1-(4-hydroxyphenyl)-2-methoxyethan-1-one
32136-81-5

1-(4-hydroxyphenyl)-2-methoxyethan-1-one synthesis

11synthesis methods
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%).
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Yield: 85%

Reaction Conditions:

with sodium hydroxide in methanol

Steps:

3 Preparation of alpha-methoxy-4-hydroxyacetophenone
EXAMPLE 3 Preparation of alpha-methoxy-4-hydroxyacetophenone 2 g of alpha-bromo-4-hydroxyacetophenone are dissolved in 11 g of methanol. 30 g of a saturated solution of sodium hydroxide in methanol (1 g NaOH/ 4.2 ml methanol) is added dropwise to the alpha-bromo-4-hydroxyacetophenone solution. After the addition is complete, the solution is added to 30 g of ice and acidified to pH 6. Alpha-methoxy-4-hydroxyacetophenone precipitates out and is filtered and dried to a greenish yellow product in about 85% yield; the product is determined by 1-H-NMR to be substantially pure.

References:

Hoechst Celanese Corporation US5107034, 1992, A

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