Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Cyclohexanol | HCID 7966 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Methyl 2-(benzamido)-4-hydroxybenzoate | HCID 57879368 | — |
| Reactant | DIAD toluene | HCID 66880968 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57879309 | HCID 57879309 | — |
Reaction Steps
0.20 mL of 40% diisopropyl azodicarboxylate /toluene was added dropwise to 1 mL of tetrahydrofuran solution containing 90 mg of methyl 2-(benzamido)-4-hydroxybenzoate, 0.035 mL of cyclohexanol and 0.10 g of triphenylphosphine at room temperature, and stirred at the same temperature for 5 hours. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to obtain 36 mg of methyl 2-(benzamido)-4-(cyclohexyloxy)benzoate as while solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07999132B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-bc7bf9808725485b991632955cb14515 |
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| Source note | uspto-grants-2011_08 |
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