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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
2,4-Dihydroxyacetophenone is a natural product isolated and purified from the root of Paeonia moutan Sim..
Synonyms: Resacetophenone; 1-(2,4-Dihydroxyphenyl)ethanone; 4-Acetylresorcinol
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Batch number can be found on the product's label following the word 'Batch'.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 89-84-9 |
Formula : | C8H8O3 |
M.W : | 152.15 |
SMILES Code : | CC(C1=CC=C(O)C=C1O)=O |
Synonyms : |
Resacetophenone; 1-(2,4-Dihydroxyphenyl)ethanone; 4-Acetylresorcinol
|
MDL No. : | MFCD00002279 |
InChI Key : | SULYEHHGGXARJS-UHFFFAOYSA-N |
Pubchem ID : | 6990 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In toluene; | EXAMPLE 31 304 g of 2,4-dihydroxy-acetophenone and 142 g of pyrrolidine are stirred in 1 l of toluene. 320 g of 1-N-pyrrolidinyl-cyclohexane are then added and the mixture is stirred for 3 hours at 25 and then for a further 3 hours at the reflux temperature. After cooling, 1 kg of ice and 1 l 4 N HCl are stirred into the dark solution. After a short time 2,2-pentamethylene-7-hydroxychroman-4-one precipitates out from the organic phase and is filtered off and rinsed with water. The toluene is separated off from the filtrate and concentrated to about 400 ml, whereupon a further fraction precipitates. Total yield 339 g (73% of the theoretical yield): melting point: 170-171. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73.0% | In ethanol;Reflux; | General procedure: solutionof acid hydrazide (0.01 mol) and appropriate benzaldehyde/acetophenone (0.01 mol) in ethanol was refluxed for 5-6 h. The precipitated title compounds were then filtered off, washed with water and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31.8% | With potassium carbonate; In acetone; for 4h;Reflux; | General procedure: To a solution of various substituted phenols (1 mmol) in dry acetone (30 mL) K2CO3 (1 mmol)and compound 3 or 4 (1 mmol) were added. After being stirred for 4 h at reflux temperature, thereaction mixture was cooled, filtered, and concentrated under vacuum. Then the residue was dilutedwith 30 mL ethyl acetate and sequentially washed with 30 mL 1 M HCl, aq. NaHCO3 solution andbrine in order. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of theresidue by chromatography on silica gel furnished target compounds. 1H-NMR, 13C-NMR and massspectroscopy (MS) of compounds 5a-m and 6a-m are shown in Supplementary Materials. |