Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Chloromethyl Methyl Ether | HCID 7864 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3-(Dimethylamino)-4-hydroxybenzaldehyde | HCID 19026982 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 19026975 | HCID 19026975 | — |
Reaction Steps
To a suspension of sodium hydride (60% in oil, 1.90 g, 47.5 mmol) in dry DMF (60 ml) was added dropwise a solution of the compound (3) (5.98 g, 36.2 mmol) obtained above in DMF (40 ml) under nitrogen atmosphere under ice-cooling. The mixture was stirred at 0° C. for 30 minutes, and thereto was added dropwise chloromethyl methyl ether (3.6 ml, 47.4 mmol). The reaction mixture was stirred at 0° C.-room temperature for 2 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The concentrate was purified by column chromatography on silica gel to give the title aldehyde compound (Compound A) as yellow liquid. Yield 7.17 g (95%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05308840 |
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| Source dataset | uspto-grants-1994_05 |
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| ORD ID | ord-8080489a48d943ccbfd906e453e3c9bf |
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| Source note | uspto-grants-1994_05 |
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