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CAS No. : | 60186-33-6 | MDL No. : | MFCD00615145 |
Formula : | C16H16O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NCOFQZRLIYPMNJ-UHFFFAOYSA-N |
M.W : | 256.30 | Pubchem ID : | 561364 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; N,N-dimethyl-formamide; at 20 - 60℃; for 3.5h; | To the solution of 3-ethoxy-4-hydroxy-benzaldehyde (83g) in N,N-dimethylformamide (400ml) was gradually added 10 M sodium hydroxide (55 ml) and then benzyl chloride (60ml) was added at a temperature under 40C. The mixture was stirred at room EPO <DP n="30"/>temperature for a half an hour and for 2 hours at 6O0C. The solution was poured into ice- cold water (2 1) and extracted with diethyl ether. The organic phase was washed with water and 5M sodium hydroxide and then it was dried and evaporated. The product was recrystallized from toluene-heptane. 1H NMR (DMSOd6): delta = 1.34 (t, 3H), 4.12 (q, 2H), 5.24 (s, 2H), 7.26 (d, IH), 7.34-7.53 (m, 7H), 9.83 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 40℃; for 2h; | To a solution of3-ethoxy-4-hydroxy-benzaldehyde (830 mg, 5 mmol) in N'N-dimethylforrnemide (5 mL)was gradually added K2CO3 (20 mg) and then PmBr (6 mmol) was added ata temperature under 40 C. The mixture was stirred at room temperature for 2 h.The solution was poured into ice-cold water (10 mL) and extracted with diethylether. The organic phase was washed with water and sodium hydroxide and then itwas dried and evaporated to obtain 18 (1.1g, 85%). Compound 18 was reacted with sophoridine using same proceduredescribed in synthesis of 11-16 to obtain 14-(4-(benzyloxy)-3-ethoxyphenylmethylene)sophoridine (20) (120 mg, 30%) |
With potassium carbonate; In acetonitrile; for 3h;Heating / reflux; | 25 g of 3-ethoxy-4-hydroxybenzaldehyde, 27 g of benzyl bromide, 25 g of potassium carbonate and 250 ml of acetonitrile were mixed, and stirred under condition of reflux for 3 hours. Then the reaction mixture was cooled to room temperature. Ethyl acetate was added to it, and solid was filtered off. The obtained organic layer was concentrated under reduced pressure, the residue was washed bymethyl=tert-butylether and hexane to obtain 36 g of 4-benzyloxy-3-ethoxybenzaldehyde.1H-NMR (CDCl3, TMS) delta (ppm): 9.82 (1H, s), 7.28-7.44 (7H, m), 6.98 (1H, d, J=8.2 Hz), 5.24 (2H, s), 4.18 (2H, q, J=7.0 Hz), 1.49 (3H, t, J=7.0 Hz) | |
With potassium carbonate; In acetonitrile; for 3h;Heating / reflux; | Reference Example 5 25 g of 3-ethoxy-4-hydroxybenzaldehyde, 27 g of benzyl bromide, 25 g of potassium carbonate and 250 ml of acetonitrile were mixed and stirred under reflux for 3 hours. After the reaction mixture was allowed to cool to room temperature, ethyl acetate was added and the mixture was filtered. The resulting filtrate was concentrated under reduced pressure. The residue was washed with tert-butyl methyl ether and hexane to obtain 36 g of 4-benzyloxy-3-ethoxybenzaldehyde. 1H-NMR (CDCl3, TMS) delta (ppm): 9.82 (1H, s), 7.28-7.44 (7H, m), 6.98 (1H, d, J = 8.2 Hz), 5.24 (2H, s), 4.18 (2H, q, J = 7.0 Hz), 1.49 (3H, t, J = 7.0 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In methanol; | EXAMPLE 17 Synthesis of 2-[(3-ethoxy-4-benzyloxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone After 6-hydroxy-2H-benzofuran-3-one 1 g and <strong>[60186-33-6]3-ethoxy-4-benzyloxybenzaldehyde</strong> 1.80 g were dissolved in methanol 75 ml, concentrated hydrochloric acid 50 ml was added, and the mixture was refluxed for 1.5 hours. The solution was cooled to room temperature, and precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60 C. for four hours under reduced pressure to obtain the desired compound 1.33 g. FAB MASS; 389 (M+1) 1H-NMR (ppm, in DMSO-d6); 1.34 (3H, t), 4.08 (3H, s), 5.14 (2H, s), 6.70-6.73 (3H, m), 6.79 (1H, s), 7.08 (1H, d, J=8.5 Hz), 7.39-7.60 (8H, m), 11.11 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.2 By the method of Example 59.1, the nitrile from Example 76.1, <strong>[60186-33-6]4-benzyloxy-3-ethoxybenzaldehyde</strong> and benzylisonitrile gave (RS)-N-benzyl-2-(4-benzyloxy-3-ethoxyphenyl)-2-(4-cyano-3-hydroxyphenylamino)-acetamide. |
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