Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | (+-)-Methyl mandelate | HCID 78066 | — |
| Reactant | HCID 14370883 | HCID 14370883 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Product | HCID 14370895 | HCID 14370895 | 47.4% |
Reaction Steps
To a dichloromethane (20 ml) solution of 4-undecyloxyphenylacetic acid (2 g, 7 mmol.) was added dropwise oxalyl chloride (1 ml). The reaction solution was stirred at 50° C. for one hour, which was then cooled, followed by concentration under reduced pressure The concentrate was dissolved in dichloromethane (10 ml), and the solution was added dropwise to a dichloromethane (10 ml) solution of methyl mandelate (1.1 g, 6.5 mmol.). To the reaction solution was added pyridine (2 ml), and the mixture was stirred at room temperature for two hours, to which was then added water (50 ml), followed by extraction with IPE. The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (developing solvent: IPE) to give methoxycarbonylphenylmethyl 4-undecyloxyphenylacetate (2-g, 1.4 g, 43%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04939274 |
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| Source dataset | uspto-grants-1990_07 |
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| ORD ID | ord-b26a2946afe34a3597f71cd2f0050878 |
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| Source note | uspto-grants-1990_07 |
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