HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1935396Generated: October 30, 2026
Dimethylformamide → Methyl 4-cyano-3-hydroxybenzoate
https://huagongshe.com/reaction/1935396
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl 3-hydroxy-4-iodobenzoate | HCID 10378812 | — |
| Reactant | Water ethylacetate | HCID 22728543 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Product | Methyl 4-cyano-3-hydroxybenzoate | HCID 16641129 | — |
Reaction Steps
A mixture of the iodide product from Step B (101 g, 0.36 mol) and zinc(II)cyanide (30 g, 0.25 mol) in 400 mL of dry DMF was degassed by bubbling argon through the solution for 20 minutes. Tetrakis(triphenylphosphine)palladium (8.5 g, 7.2 mmol) was added, and the solution was heated to 80° C. for 4 hours. The solution was cooled to room temperature, then stirred for an additional 36 hours. The reaction was poured into EtOAc water, and the organic layer was washed with brine (4×), dried (Na2SO4), and concentrated in vacuo to provide the crude product. Purification by column chromatography through silica gel (30%-50% EtOAc/hexane) provided the titled product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06387903B1 |
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| Source dataset | uspto-grants-2002_05 |
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| ORD ID | ord-5c9eb83a3a2347ba80f030e04305365e |
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| Source note | uspto-grants-2002_05 |
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