Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrogallol | HCID 1057 | — |
| Reactant | 1,2-Dibromoethane | HCID 7839 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 20036523 | HCID 20036523 | 36% |
Reaction Steps
A suspension of pyrogallol (126 g) and potassium carbonate (138 g) in dimethylformamide (500 mL) was stirred at 80° C. for 2 hours. 1,2-Dibromoethane (188 g) was then added dropwise over a 4 hour period and the resulting mixture was stirred at 80° C. overnight. Upon cooling, the mixture was filtered, and the filtrate was evaporated, dissolved in water (200 mL) and acidified with concentrated hydrochloric acid. The resulting mixture was extracted with toluene. The orgainc extract was washed with water, dried over sodium sulfate, filtered and evaporated. Fractional distillation (82° C., 0.05 mm) afforded 54.7 g of 2,6-ethylenedioxyphenol, as an oil. Similary, using the above procedure but substituting 1,3-dibromopropane for 1,2-dibromoethane 2,3-propylenedioxyphenol, mp 110°-111° C. was prepared.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04840965 |
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| Source dataset | uspto-grants-1989_06 |
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| ORD ID | ord-6cede5e39c924b3da17fd36cef9d0e63 |
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| Source note | uspto-grants-1989_06 |
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