A kind of synthetic method of 3-hydroxymethyl tetrahydrofuran
A technology of hydroxymethyltetrahydrofuran and synthetic methods, applied in the direction of organic chemistry, etc., can solve the problems of long synthetic route, complicated production operation, high risk, etc., and achieve the effect of mild reaction conditions, simple process operation and short synthetic route
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Embodiment 1
[0018] Synthesis of tetrahydrofuran-3-carbaldehyde:
[0019] Add 2,5-dihydrofuran (84.11 g, 1.2 mol), rhodium dicarbonyl acetylacetonate (1.05 g, 4 mmol) and triphenylphosphine (3.15 g, 12 mmol) in the reaction kettle, and use N 2 After replacing deoxygenation, 2 MPa H is introduced 2 and 2 MPa CO at 60 o C was stirred and reacted for 6 h, cooled to room temperature, slowly vented, and filtered to obtain 119.42 g of tetrahydrofuran-3-carbaldehyde with a yield of 99.4%. 1 H NMR (400 MHz, CDCl 3 ) δ 9.64 (1H), 4.09-4.06 (q, J = 4.0 Hz, 1H),3.90-3.93 (m, 2H), 3.77-3.71 (q, J = 8.0 Hz, 1H), 3.07-3.01 (m, 1H), 2.22-2.06 (m, 2H); 13 C NMR (101 MHz, CDCl 3 ) δ 200.96, 68.00, 67.36, 51.15, 26.59.
[0020] Synthesis of 3-hydroxymethyltetrahydrofuran:
[0021] Dissolve tetrahydrofuran-3-carbaldehyde (50.06 g, 0.5 mol) in ethanol (400 mL), then cool to 0 o C. Add sodium borohydride (18.92 g, 0.5 mol) to the above solution in batches, after the addition is complete, stir the re...
Embodiment 2
[0023] Synthesis of tetrahydrofuran-3-carbaldehyde:
[0024] Add 2,5-dihydrofuran (84.11 g, 1.2 mol), rhodium dicarbonyl acetylacetonate (0.31 g, 1.2 mmol) and triphenylphosphine (1.26 g, 4.8 mmol) in the reaction kettle, and use N 2 After replacing deoxygenation, 2 MPa H is introduced 2 and 2 MPa CO at 60 o C was stirred and reacted for 8 h, cooled to room temperature, slowly vented, and filtered to obtain 118.58 g of tetrahydrofuran-3-carbaldehyde with a yield of 98.7%.
[0025] Synthesis of 3-hydroxymethyltetrahydrofuran:
[0026] Dissolve tetrahydrofuran-3-carbaldehyde (50.06 g, 0.5 mol) in methanol (400 mL), then cool to 0 o C. Add sodium borohydride (22.69 g, 0.6 mol) to the above solution in batches, after the addition is complete, stir the reaction at room temperature for 2 h until the raw material disappears, then slowly add concentrated hydrochloric acid (51 mL) dropwise to adjust the pH value to neutral , a large amount of white solid precipitated, filtered, and...
Embodiment 3
[0028] Synthesis of tetrahydrofuran-3-carbaldehyde:
[0029] Add 2,5-dihydrofuran (84.11 g, 1.2 mol), rhodium dicarbonyl acetylacetonate (0.06 g, 0.24 mmol) and triphenylphosphine (0.25 g, 0.96 mmol) into the reaction kettle, and use N 2 After replacement deoxygenation, 2 MPa H is introduced 2 and 2 MPaCO at 80 o C was stirred and reacted for 24 h, cooled to room temperature, slowly vented, and filtered to obtain 116.66 g of tetrahydrofuran-3-carbaldehyde with a yield of 97.1%.
[0030] Synthesis of 3-hydroxymethyltetrahydrofuran:
[0031] Dissolve tetrahydrofuran-3-carbaldehyde (50.06 g, 0.5 mol) in methanol (400 mL), then cool to 0 oC. Add sodium borohydride (22.69 g, 0.6 mol) to the above solution in batches. After the addition is complete, stir the reaction at room temperature for 5 h until the raw material disappears, then slowly add concentrated hydrochloric acid (51 mL) to adjust the pH value to neutral , a large amount of white solid precipitated, filtered, and the...
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