Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | p-Toluenesulfonate | HCID 85570 | — |
| Reactant | Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester | HCID 3084696 | — |
| Reactant | HCID 19004350 | HCID 19004350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 53858000 | HCID 53858000 | 42.4% |
Reaction Steps
A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.27 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.303 g), stirred for 15 minutes and treated with the tosylate prepared from 2-(cyclooctyloxy)ethanol (2.18 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-ethyl acetate; 80:20:2) to provide 1.0 g of pure 4-[[2-(cyclooctyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester as an oil.
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-9f656e2d5e534349b99ee8508103d9d0 |
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| Source note | uspto-grants-1994_09 |
|---|
