Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 2-Methoxy-4-nitrobenzaldehyde | HCID 2759599 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 66811313 | HCID 66811313 | 95.5% |
Reaction Steps
To a stirred solution of 2-methoxy-4-nitro-benzaldehyde (4.61 g, 25.4 mmol) in toluene (51 mL), was added p-toluene sulfonic acid (483 mg, 2.54 mmol), followed by ethylene glycol (2.83 mL, 50.8 mmol). After heating the reaction mixture at 50° C. for 12 h, additional p-toluene sulfonic acid (483 mg, 2.54 mmol) and ethylene glycol (2.83 mL, 50.8 mmol) were added. After an additional 12 h, the solvent was removed under reduced pressure, and the resulting residue was dissolved in dichloromethane (50 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution (25 mL), dried over sodium sulfate, filtered and the solvent removed under reduced pressure to give the title compound as a yellow solid (5.46 g, 95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07569586B2 |
|---|
| Source dataset | uspto-grants-2009_08 |
|---|
| ORD ID | ord-506965e008b448c2892a0d10e760b18d |
|---|
| Source note | uspto-grants-2009_08 |
|---|