Methyl 3,5-diisopropoxy-4-methoxybenzoate → Methyl 3,4-methylenedioxy-5-methoxybenzoate
Reaction equation
C(OC1C=C(B(O)O)C=C(OC(C)C)C=1OC)(C)C.[CH:20]([O:23][C:24]1[CH:25]=[C:26]([CH:31]=[C:32]([O:36][CH:37](C)C)[C:33]=1[O:34]C)[C:27]([O:29][CH3:30])=[O:28])(C)C>>[CH3:20][O:23][C:24]1[CH:25]=[C:26]([CH:31]=[C:32]2[O:36][CH2:37][O:34][C:33]=12)[C:27]([O:29][CH3:30])=[O:28].[CH3:20][O:23][C:24]1[CH:25]=[C:26]([CH:31]=[C:32]2[O:36][CH2:37][O:34][C:33]=12)[C:27]([OH:29])=[O:28]Participants
Procedure
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%).
Sources & evidence
- ORD record
- ord-2bfed885d3804bd19e3d29eed6ec3d45
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06706703B2
Reaction notes
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