Synthetic method of 6-hydroxyl-2-methylbenzofuran compound
A compound and acylation technology, which is applied in the field of synthesizing 6-hydroxy-2-methylbenzofuran compounds, can solve the problems of cumbersome reaction process, etc., and achieve the effect of simple reaction route, mild reaction conditions and low cost
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Embodiment 1
[0055] a) Synthesis of 2-chloro-1-(2,4-dihydroxy-phenyl)-propan-1-one
[0056]
[0057] Add resorcinol (110g, 1mol) and ethylene dichloride (1100ml) in the reaction flask, replace 3 times with nitrogen, reduce the internal temperature to 0~5°C, add anhydrous aluminum trichloride (134g, 1mol ). Controlling the internal temperature at 0-5°C, slowly added 2-chloro-propionyl chloride (127 g, 1 mol) dropwise. After the dropwise addition, the temperature was naturally raised to room temperature (15-25° C.), stirred overnight, and the reaction was monitored by LC-MS. After the reaction was completed, the reaction solution was poured into 2 L of crushed ice, and a large amount of yellow solids were precipitated. Suction filtration, wash the filter cake with water until neutral. After drying under reduced pressure at 40-50°C, 151.3 g of the title compound was obtained as a pale yellow solid with a purity of 99.5% and a yield of 75.6%.
[0058] 1 H NMR (400MHz, CD 3 OD) δ7.78(d...
Embodiment 2
[0068] Synthesis of 2-bromo-1-(2,4-dihydroxy-phenyl)-propan-1-one
[0069]
[0070] The reaction conditions were the same as in Example 1a), and the title compound was obtained as a pale yellow solid with a purity of 99.5% and a yield of 42%.
[0071] 1 H NMR (400MHz, CD 3 OD) δ7.79(d, J=9.0Hz, 1H), 6.39(dd, J=8.9, 2.4Hz, 1H), 6.29(d, J=2.4Hz, 1H), 5.53(q, J=6.6Hz , 1H), 1.81 (d, J=6.6Hz, 3H).
Embodiment 3
[0073] a) Synthesis of 2-chloro-1-(2,4-dihydroxy-phenyl)-butane-1-one
[0074]
[0075] The reaction conditions were the same as in Example 1a), and the title compound was obtained as a pale yellow solid with a purity of 99% and a yield of 40.6%.
[0076] 1 H NMR (400MHz, CD 3 OD) δ7.78 (d, J=8.8Hz, 1H), 6.39 (dd, J=8.9, 2.4Hz, 1H), 6.28 (d, J=2.4Hz, 1H), 5.28 (dd, J=7.8, 6.0Hz, 1H), 2.20-2.04(m, 1H), 2.03-1.89(m, 1H), 1.03(t, J=7.4Hz, 3H).
[0077] b) Synthesis of 2-ethyl-6-hydroxyl-benzofuran-3-one
[0078]
[0079] The reaction conditions were the same as in Example 1b), and the title compound was obtained as a white solid with a purity of 99.3% and a yield of 84.2%.
[0080] 1 H NMR (400MHz, CD 3 OD) δ7.46 (d, J=8.5Hz, 1H), 6.56 (dd, J=8.6, 2.0Hz, 1H), 6.44 (d, J=2.0Hz, 1H), 4.56 (dd, J=7.0, 4.5Hz, 1H), 2.04-1.94(m, 1H), 1.81-1.71(m, 1H), 0.97(t, J=7.4Hz, 3H).
[0081] c) Synthesis of 6-hydroxyl-2-ethyl-benzofuran
[0082]
[0083] The reaction conditions...
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