HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2225694Generated: October 30, 2026
Sodium hydride → 4-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester
https://huagongshe.com/reaction/2225694
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester | HCID 3084696 | — |
| Reactant | 2-(3-Bromopropyl)naphthalene | HCID 11817529 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester | HCID 54003296 | 20.5% |
Reaction Steps
A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.01 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.262 g), stirred for 15 minutes and treated with 2-(3-bromopropyl)naphthalene (1.7 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 4:1) and crystallized from diethyl ether-hexane to provide 0.4 g of 4-[[3-(2-naphthalenyl) propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 97°-99° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05344843 |
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| Source dataset | uspto-grants-1994_09 |
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| ORD ID | ord-1d670dee82d34791a1b1a8751e413fca |
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| Source note | uspto-grants-1994_09 |
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