Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Benzene, 1,3-diphenoxy- | HCID 76911 | — |
| Reactant | HCID 15872348 | HCID 15872348 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Reactant | HCID 178418348 | HCID 178418348 | — |
| Reactant | HCID 178506763 | HCID 178506763 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23714060 | HCID 23714060 | — |
Reaction Steps
The desired 2,6-diphenoxybenzoic acid can be prepared as illustrated in equation 1 ##STR4## In this method, 1,3-diphenoxybenzene is caused to react with an alkyllithium compound ZLi where Z is alkyl of 1 to 4 carbon atoms or phenyl, for example, methyllithium or butyllithium, in an ether-type solvent such as diethyl ether or tetrahydrofuran for 0.5 to 3 hours at 25°-100°, preferably at the boiling point of the solvent. The resulting intermediate, 2,6-diphenoxyphenyllithium, is added to an excess of solid carbon dioxide, or a mixture of solid carbon dioxide in ether, and the mixture is allowed to warm to room temperature to yield lithium 2,6-diphenoxybenzoate. Addition of a mineral acid, HX, such as hydrochloric acid or sulfuric acid, yields 2,6-diphenoxybenzoic acid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04191554 |
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| Source dataset | uspto-grants-1980_03 |
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| ORD ID | ord-4a365c3846f04779b4f7e85a0258598e |
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| Source note | uspto-grants-1980_03 |
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