Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl formate | HCID 8025 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethyl (4-chlorophenyl)acetate | HCID 84177 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 13174739 | HCID 13174739 | 78.4% |
Reaction Steps
Then, 4.19 g of sodium hydride (60% in oil) was suspended in 150 ml of tetrahydrofuran, to which a solution of 19.0 g of ethyl 4-chlorophenylacetate in 150 ml of tetrahydrofuran was added dropwise at 5° to 10° C. After stirring at room temperature for 1.5 hours, 8.42 g of ethyl formate was added, and the mixture was further stirred at room temperature for 4.5 hours. After completion of the reaction, the reaction mixture was cooled to ice temperature, neutralized by the addition of diluted hydrochloric acid, and concentrated. The residue was subjected to phase separation with ethyl acetate-water, and the organic layer was dried and then concentrated. The residue was subjected to silica gel chromatography, which afforded 17.0 g of ethyl 2-(4'-chlorophenyl)-2-formylacetate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06100257 |
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| Source dataset | uspto-grants-2000_08 |
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| ORD ID | ord-1a828f135bd146e3926270c8b92e0d9f |
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| Source note | uspto-grants-2000_08 |
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