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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.
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| CAS No. : | 626-77-7 |
| Formula : | C9H18O2 |
| M.W : | 158.24 |
| SMILES Code : | CCCCCC(OCCC)=O |
| English Name : | Propyl hexanoate |
| MDL No. : | MFCD00053803 |
| InChI Key : | HTUIWRWYYVBCFT-UHFFFAOYSA-N |
| Pubchem ID : | 12293 |
* 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 pyridine |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 93% | Stage #1: hexanoic acid With dmap In tetrahydrofuran; dichloromethane at 25℃; for 0.166667h; Inert atmosphere; Stage #2: propan-1-ol In tetrahydrofuran; dichloromethane at 25℃; for 0.25h; Inert atmosphere; | |
| 89% | With pyridine; N,N'-dibromo-N,N'-(1,2-ethanediyl)bis(p-toluenesulfonamide); triphenylphosphine In dichloromethane at 20℃; | |
| 77% | at 150℃; for 2.5h; |
| With sulfuric acid In 1,4-dioxane at 60℃; | ||
| With sulfuric acid In 1,4-dioxane at 60℃; | ||
| With toluene-4-sulfonic acid; benzene | ||
| 82 %Chromat. | With rapeseed lipase acetone powder In hexane at 40℃; for 48h; Enzymatic reaction; | |
| With polyisobutylene bound 3-sulfoanisole at 70℃; for 5h; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With diethylazodicarboxylate In tetrahydrofuran |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sulfuric acid; water In 1,4-dioxane at 60℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 79% | With chloro-trimethyl-silane for 2h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Capronsaeure, Propen, Methansulfonsaeure, Druck; | ||
| Capronsaeure, Propen, BF3*Et2O, Druck; | ||
| Capronsaeure, Propen, ZnCl2, Druck; |
| Exemplary of compounds represented by formula II are, for example ... propyl acetate hexyl acetate methyl propanoate ethyl butanoate propyl hexanoate methyl dodecanoate hexyl dodecanoate |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With sulfuric acid |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 81% | With molybdenum(V) chloride In dichloromethane at 80℃; for 1h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 81% | With molybdenum(V) chloride In 1,2-dichloro-ethane at 80℃; for 1h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With Ce0.5Zr0.5O2 at 349.84℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88 %Chromat. | With cerium(IV) oxide at 160℃; for 32h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium <i>tert</i>-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; for 16h; Inert atmosphere; Glovebox; Autoclave; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 89% | With octadecyltriethoxysilane-treated high-silica Hβ-20 zeolite In water at 130℃; for 24h; | 2.4. Catalytic tests General procedure: The heterogeneous catalysts, stored under ambient conditions,were used for catalytic reactions without any pretreatment. Typically,ester (1 mmol), 1 mL H2O and 10 mg of catalysts and a magneticstarter bar were added to a reaction vessel (Pyrex pressuretube, 13 mL), and the mixture was heated at 130 °C under air withstirring at 300 rpm. For the catalytic tests in Table 1 and kineticstudy, conversions and yields were determined by GC-FID usingn-dodecane as an internal standard as follows. After completionof the reaction, acetone (7 mL) was added to the mixture, andthe catalyst was separated by centrifugation. Then, n-dodecane(0.2 mmol) was added to the reaction mixture, and the mixturewas analyzed by GC-FID and GC-MS. The GC-FID sensitivities ofthe products were determined using commercial carboxylic acidsor the isolated products after the reaction. For some of the productsin Tables 2 and 3, we determined isolated yields of the carboxylicacids as follows. After the filtration of the catalyst, followed bywashing the catalyst with acetone (6 mL), and by evaporation,the product was isolated by column chromatography using silicagel 60 (spherical, 63-210 μm, Kanto Chemical Co. Ltd.) with hexane/ethyl acetate (60/40-80/20) as the eluting solvent, followedby analyses by 1H NMR, 13C NMR and GC-MS equipped with thesame column as GC-FID. |
| 89% | With pyrographite; sodium hydroxide In water at 20℃; for 24h; | General procedure for the alkaline hydrolysis of ester 1 mediated by activated charcoal General procedure: A solution of NaOH (120 mg, 3.0 mmol) in water (2.0 mL) was added to a mixture of ester 1g (284 mg, 2.0 mmol) and activated charcoal (400 mg) in a 10 mL flask. The mixture was stirred at 700 rpm at room temperature for 3 minutes. After stirring the mixture at 400 rpm for 24 h, the mixture was acidified with 3 M-sulfuric acid and Et2O (10 mL) was added. Activated charcoal was removed by filtration and washed with ether. The mixture was extracted with ether three times. The combined extracts were washed with water (2 mL×2), dried, and evaporated. The residue was purified by column chromatography on silica gel using heptane-acetone (3 : 1) as eluent to give 2g (233 mg, 91%). When the products 2 were solids, the next work-up procedure without organic solvents is possible; A solution of NaOH (120 mg, 3.0 mmol) in water (2.0 mL) was added to a mixture of ester 1b (272 mg, 2.0 mmol) and activated charcoal (400 mg) in a 10 mL flask. The mixture was stirred at 700 rpm at room temperature for 2 minutes. After stirring at 400 rpm for 24 h, activated charcoal was removed by filtration and washed with water. The filtrate was acidified with 6 M-Hydrochloric acid. The resulting precipitate was filtered and washed with water (2 mL×2) to give 2b (180 mg, 74%). Compound 2b was recrystallized from heptane. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 60 % ee | With baeyer-villiger monooxygenases 2 In ethanol at 24℃; for 24h; Enzymatic reaction; |