Methyl 3,5-diisopropoxy-4-methoxybenzoate → Methyl 3,4-methylenedioxy-5-methoxybenzoate

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Reaction Steps

Synthesis of the title compound from methyl 3-methoxy-4,5-methylenedioxybenzoate was carried out by applying the synthetic procedure of 3,5-diisopropoxy-4-methoxyphenylboronic acid from methyl 3,5-diisopropoxy-4-methoxybenzoate in Reference Example 6. From methyl 3-methoxy-4,5-methylenedioxybenzoate (4.30 g, 20.5 mmol), 3-methoxy-4,5-methylenedioxybenzoic acid (3.00 g) was obtained as colorless prisms (melting point: 215.0-216.0° C.) (yield: 71%). From 3-methoxy-4,5-methylenedioxybenzoic acid (2.50 g, 12.7 mmol), 3-methoxy-4,5-methylenedioxy-1-nitrobenzene was obtained as a pale yellow amorphous powder (1.26 g, yield: 50%). From 3-methoxy-4,5-methylenedioxy-1-nitrobenzene (1.26 g, 16.4 mmol), 1-iodo-3-methoxy-4,5-methylenedioxybenzene was obtained as pale yellow needles (melting point: 71.0-72.0° C.) (1.08 g, yield: 61%). From 1-iodo-3-methoxy-4,5-methylenedioxybenzene (750.0 mg, 2.70 mmol), the title compound was obtained as a colorless crystalline powder (melting point: 279.0-281.0° C.) (347.0 mg, yield: 66%).

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