Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3,4,5-Trimethoxybenzaldehyde | HCID 6858 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Catalyst | Benzyl triethylammonium chloride | HCID 66133 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 14451560 | HCID 14451560 | — |
Reaction Steps
A mixture of potassium cyanide (41.5 g), triethylbenzylammonium chloride (5.23 g), water (130 ml) and dichloromethane (150 ml) was cooled to 0° C. To the vigorously stirred mixture, a solution containing the 3,4,5-trimethoxy-benzaldehyde (100.0 g) and acetic anhydride (52.1 g) in dichloromethane (150 ml) was added drop wise at 0° C. during 30 minutes. The stirring was continued at 0° C. for 30 minutes and then at ambient temperature for one hour. The organic phase was separated, dried and concentrated to dryness, leaving crude 3,4,5-trimethoxyphenyl-α-acetoxyacetonitrile. Crystallization from ethanol-water afforded the pure product (104 g), m.p. 65-66° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08044067B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-0174de7a3e60410da03caa587d376b01 |
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| Source note | uspto-grants-2011_10 |
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