HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → 5-Methoxy-2-methylbenzene-1,3-diol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Chloromethyl Methyl Ether | HCID 7864 | — |
| Reactant | Bis(methoxymethyl)ether | HCID 12362 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-Methoxy-1,3-bis(methoxymethoxy)-2-methylbenzene | HCID 25138785 | — |
| Reactant | Methyl 4-acetoxy-3-(3-methylbut-2-enyl)benzoate | HCID 57940298 | — |
| Reactant | Methyl 4-acetoxy-3-allylbenzoate | HCID 67094163 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Methoxy-2-methylbenzene-1,3-diol | HCID 238769 | — |
Reaction Steps
The preparation of intermediate 6 is described and illustrated below. The coumarin phenol 7 was converted to the methoxymethyl ether using methoxymethyl chloride and Hunig's base in Dimethylformamide. The free aniline, liberated through hydrogenolysis with 10% Pd/C and hydrogen in tetrahydrofuran from 7, was coupled with acid chloride 9 to give benzamide 10. Subsequent cleavage of the methoxymethyl ether with 4N hydrochloride in dioxane provided phenol 6 in high yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09120774B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-d3ff04d5260d4fc8983da3b14a5af1ea |
| Source note | uspto-grants-2015_09 |