HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-Dimethylphenol → 2-Phenoxybenzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-Dimethylphenol | HCID 10687 | — |
| Reactant | Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- | HCID 112414 | — |
| Reactant | 3-BROMO-2-IODOBENZOIC ACID | HCID 11232662 | — |
| Catalyst | Cuprous chloride | HCID 62652 | — |
| Product | 2-Phenoxybenzoic acid | HCID 75237 | — |
Reaction Steps
As shown in the Scheme, at the presence of 10% by mole of CuCl and 10% by mole of tris(2-(2-methoxyethoxy)ethyl) amine (TDA-1), 3-bromo-2-iodo benzoic acid was contacted with 2,3-dimethylphenol to yield phenoxybenzoic acid. Without purification, the phenoxybenzoic acid was directly dehydrated and cyclized by reagents such as sulfuric acid, methanesulfonic acid, polyphosphoric acid, or polyphosphate to yield dimethylxanthone. Diethyl malonate was arylated by the dimethylxanthone under catalysis of palladium to yield 5,6-dimethylxanthone-4-ethyl acetate which was hydrolyzed to yield DMXAA.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08350065B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-1f8b6ca031394897a4c4a145ec3cbca5 |
| Source note | uspto-grants-2013_01 |