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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.
8-Carboxyoctanol is an alcohol derivative with a carboxylic acid group at the 8th carbon. It is used as a building block for the synthesis of complex molecules and in polymer chemistry.
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CAS No. : | 3788-56-5 |
Formula : | C9H18O3 |
M.W : | 174.24 |
SMILES Code : | OCCCCCCCCC(O)=O |
MDL No. : | MFCD00792445 |
InChI Key : | AFZMICRBFKZNIH-UHFFFAOYSA-N |
Pubchem ID : | 138052 |
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 |
---|---|---|
46% | With sulfuric acid; for 5.0h;Reflux; | To a solution of <strong>[3788-56-5]9-hydroxynonanoic acid</strong> (2) (1.0 g, 5.74 mmol, 1.0 eq) in methanol (30 mL) was added sulfuric acid (1 mL). The reaction mixture was heated to reflux for 5 h. Then the mixture was concentrated under reduced pressure and the residue was diluted with water (15 mL) and ethyl acetate (10 mL). The aqueous layer was back-extracted with additional ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine and dried over anhydrous Na2SC>4. The solvent was removed under reduced pressure and the crude was purified by column chromatography (PE/EA (petroleum ether/ethyl acetate) = 10: 1) to give methyl 9-hydroxynonanoate (3) (500 mg, 46%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium tetrahydroborate; In 1,4-dioxane; at 0 - 20℃; | A solution of 0.8 g (4.65 mmol) of 7 in dioxane (8 mL) was treated with 0.2 g (50 mmol) of sodium borohydride in small portions with cooling in ice-water. the mixture then stirred at room temperature overnight, until TLC monitoring indicated completion and poured over crushed ice. Acidify the mixture by HCl 37% to consume the excess NaBH4. The product was extracted with 3 ×40 mL ether and The organic layers were combined, washed with water (1 × 30 mL), brine (1 × 30mL), and dried over Na2SO4. The solvent removed under reduced pressure and then purified by column chromatography (1:1 hexanes: ethyl acetate) to give pure 1 as a white solid (460 g, 2.64 mmol, 56 %). m.p. 51C. IR spectrum (cm-1): 3334, 2931, 2852, 1692 cm-1. 1H NMR (300 MHz,CDCl3) delta 6.07 (m, 2H, CH2OH and COOH), 3.63 (t, 2H, J = 6.6 Hz, CH2OH), 2.33 (t, 2H, J = 7.5Hz, CH2COOH), 1.62 (m, 4H, CH2CH2CH2OH and CH2CH2COOH), 1.25-1.32 (m, 8H, CH2). 13CNMR (75 MHz, CDCl3): delta 179.2 (s, COOH), 63.5 (t, CH2OH), 34.3, 32.9, 29.5, 29.3, 26.0, 25.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Any omega-hydroxy acid which falls within Formula V may be synthesised according to inventive processes A and B. Examples of omega-hydroxy acids that may be synthesised include, but are not limited to: 6-hydroxy hexanoic acid 7-hydroxy heptanoic acid 8-hydroxy octanoic acid 9-hydroxy nonanoic acid 10-hydroxy decanoic acid 11-hydroxy undecanoic acid 2,25-dihydroxy dihydroxy pentacosanoic acid 12-hydroxy dodecanoic acid 14-hydroxy tetradecanoic acid ... |