HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2225634Generated: October 31, 2026
Sodium hydride → 4-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester
https://huagongshe.com/reaction/2225634
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester | HCID 3084696 | — |
| Reactant | 1-(3-Bromopropyl)-4-fluorobenzene | HCID 14737133 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester | HCID 54198850 | 36.8% |
Reaction Steps
A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.63 g) in dimethylformamide (20 mL) under argon was treated with 55% sodium hydride (0.394 g), stirred for 15 minutes and treated with 4-fluorophenylpropyl bromide (1.25 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified on HPLC (dichloromethane-hexane; 4:1) and crystallized from diethyl etherhexane to provide 0.67 g of 4-[[3-(4-fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 42°-43° 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-53fb738e98ef4f3985930072631bae18 |
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| Source note | uspto-grants-1994_09 |
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