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CCOC1=C(C=CC(=C1)C=O)OC(C)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-ethoxy-4-propan-2-yloxybenzaldehyde |
|---|---|
| IUPAC Name | — |
| CAS Number | 284044-35-5 |
| Database ID | 874730 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-ethoxy-4-propan-2-yloxybenzaldehyde (CAS 284044-35-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 874730
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-24aa2ae97c874a3ca444bcbff9d27e03Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8a8a6c15d38840eea4779c4781c1add3Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Ethoxy-4-isopropoxybenzaldehyde (WO 2004072101) (24 g, 115 mmol) was dissolved in a 7N MeOH solution of ammonia (200 mL) and the whole was cooled to 0° C. Trimethylsilyl cyanide (24 mL, 180 mmol) was added and the reaction mixture was stirred overnight with gradual warming to rt. The reaction product was concentrated to provide 2-amino-2-(3-ethoxy-4-isopropoxyphenyl)acetonitrile (29 g, 100%) as a yellow oil. The oil (23 g) was dissolved in ethyl ether (460 mL), cooled to 0° C., and HCl (g) was bubbled through the solution for 5 min. The resulting precipitate was filtered and dried on the high vac to provide Intermediate 13A (19 g, 72%) as a yellow solid. with gradual warming to rt The reaction product was concentrated
Source ID: ord-7bf2923947a04d6f856f0cc88b33b4bfConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Ethoxy-4-isopropoxybenzaldehyde (WO 2004072101) (24 g, 115 mmol) was dissolved in a 7N MeOH solution of ammonia (200 mL) and the whole was cooled to 0° C. Trimethylsilyl cyanide (24 mL, 180 mmol) was added and the reaction mixture was stirred overnight with gradual warming to rt. The reaction product was concentrated to provide 2-amino-2-(3-ethoxy-4-isopropoxyphenyl)acetonitrile (29 g, 100%) as a yellow oil. The oil (23 g) was dissolved in ethyl ether (460 mL), cooled to 0° C., and HCl (g) was bubbled through the solution for 5 min. The resulting precipitate was filtered and dried on the high vac to provide Intermediate 13A (19 g, 72%) as a yellow solid. with gradual warming to rt The reaction product was concentrated
Source ID: ord-7bf2923947a04d6f856f0cc88b33b4bfConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Ethoxy-4-isopropoxybenzaldehyde (WO 2004072101) (24 g, 115 mmol) was dissolved in a 7N MeOH solution of ammonia (200 mL) and the whole was cooled to 0° C. Trimethylsilyl cyanide (24 mL, 180 mmol) was added and the reaction mixture was stirred overnight with gradual warming to rt. The reaction product was concentrated to provide 2-amino-2-(3-ethoxy-4-isopropoxyphenyl)acetonitrile (29 g, 100%) as a yellow oil. The oil (23 g) was dissolved in ethyl ether (460 mL), cooled to 0° C., and HCl (g) was bubbled through the solution for 5 min. The resulting precipitate was filtered and dried on the high vac to provide Intermediate 13A (19 g, 72%) as a yellow solid. with gradual warming to rt The reaction product was concentrated
Source ID: ord-7bf2923947a04d6f856f0cc88b33b4bfConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Ethoxy-4-isopropoxybenzaldehyde (WO 2004072101) (24 g, 115 mmol) was dissolved in a 7N MeOH solution of ammonia (200 mL) and the whole was cooled to 0° C. Trimethylsilyl cyanide (24 mL, 180 mmol) was added and the reaction mixture was stirred overnight with gradual warming to rt. The reaction product was concentrated to provide 2-amino-2-(3-ethoxy-4-isopropoxyphenyl)acetonitrile (29 g, 100%) as a yellow oil. The oil (23 g) was dissolved in ethyl ether (460 mL), cooled to 0° C., and HCl (g) was bubbled through the solution for 5 min. The resulting precipitate was filtered and dried on the high vac to provide Intermediate 13A (19 g, 72%) as a yellow solid. with gradual warming to rt The reaction product was concentrated
Source ID: ord-7bf2923947a04d6f856f0cc88b33b4bfConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-24aa2ae97c874a3ca444bcbff9d27e03Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8a8a6c15d38840eea4779c4781c1add3Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 3-ethoxy-4-isopropoxybenzaldehyde (1.78 g, 8.55 mmol), 4-aminobenzonitrile (1.01 g, 8.55 mmol), and 5 g 4 A molecular sieves in 20 mL toluene was refluxed with azeotropic removal of water for 2 h. The mixture was filtered and concentrated to afford 2.29 g of Intermediate 1.1 as a pale yellow solid. The mixture was filtered concentrated
Source ID: ord-43619eab10ad447689bc76ff2756adb8Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 141A (7.42 g, 35:6 mmol) and 4-cyanoaniline (4.21 g, 35.6 mmol) in methanol (120 mL) was stirred at 60° C. for 2 h. The reaction was cooled to 0° C. and p-toluenesulfonylmethyl isocyanide (6.95 g, 35.6 mmol) was added followed by dropwise addition of boron trifluoride etherate (13.5 mL, 107 mmol). After stirring for 30 min at 0° C., the reaction was allowed to warm to rt and stirring was continued for 2 h. Water (4 mL) was added and bright yellow precipitate was observed after stirring for 2 days. The solvent was removed and the residue was redissolved in ethyl acetate. The precipitate was filtered and dried to give 7.89 g of 141B as a white solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.18-1.20 (m, 6H) 1.28 (t, J=6.98, 3H) 3.62 (s, 3H) 3.90-3.98 (m, 2H) 4.40-4.50 (m, 1H) 5.06 (s, 1H) 6.59 (d, J=8.90 Hz, 2H) 6.80-7.00 (m, 3H) 7.29 (d, J=8.90 Hz, 2H). to warm to rt stirring was continued for 2 h after stirring for 2 days The solvent was removed the residue was redissolved in ethyl acetate The precipitate was filtered dried
Source ID: ord-ec75ae4ee7e543689f4301fe7ad63f86Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 3-ethoxy-4-hydroxybenzaldehyde (20.0 g, 120 mmol) in dimethylformamide (250 mL) was added potassium carbonate (33.1 g, 240 mmol) then 2-iodopropane (18 mL, 180 mmol). The reaction mixture was heated to 45° C. and stirred for 3 h. After cooling to rt, the crude reaction mixture was extracted with ethyl acetate (3×). The combined extracts were then washed with water (3×) then brine and dried over sodium sulfate. The solvent was removed to give 24 g of 141A as a yellow oil. LC-MS: 231.17 (M+Na)+. After cooling to rt the crude reaction mixture was extracted with ethyl acetate (3×) The combined extracts were then washed with water (3×) brine and dried over sodium sulfate The solvent was removed
Source ID: ord-7024f68d15474dd3b07bf62a494df3a7Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3-Ethoxy-4-isopropoxybenzaldehyde (WO 2004072101) (24 g, 115 mmol) was dissolved in a 7N MeOH solution of ammonia (200 mL) and the whole was cooled to 0° C. Trimethylsilyl cyanide (24 mL, 180 mmol) was added and the reaction mixture was stirred overnight with gradual warming to rt. The reaction product was concentrated to provide 2-amino-2-(3-ethoxy-4-isopropoxyphenyl)acetonitrile (29 g, 100%) as a yellow oil. The oil (23 g) was dissolved in ethyl ether (460 mL), cooled to 0° C., and HCl (g) was bubbled through the solution for 5 min. The resulting precipitate was filtered and dried on the high vac to provide Intermediate 13A (19 g, 72%) as a yellow solid. with gradual warming to rt The reaction product was concentrated
Source ID: ord-7bf2923947a04d6f856f0cc88b33b4bfPubChem References
These sources are listed in the compound's public database record.
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