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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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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'.
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CAS No. : | 78-69-3 |
Formula : | C10H22O |
M.W : | 158.28 |
SMILES Code : | CCC(O)(C)CCCC(C)C |
MDL No. : | MFCD00004482 |
InChI Key : | DLHQZZUEERVIGQ-UHFFFAOYSA-N |
Pubchem ID : | 6548 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-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 Amberlyst-15; In dichloromethane; for 2.5h;Reflux; | General procedure: Amberlyst-15 (dry) (75 mg) was added to a dichloromethane solution (15 mL) of 4-(2-hydroxypropan-2-yl)-1-methylcyclohexanol (1a, trans-terpin) (75 mg; 0.43 mmol). The reaction was stirred at room temperature (rt) and monitored by TLC [diethyl ether/hexane (3:1) as eluent] until the verification of the disappearance of the reagent (3.5 h). The Amberlyst-15 was removed by filtration and the solvent was evaporated under reduced pressure at rt to give a residue. Dichloromethane (30 mL) was added to re-dissolve this residue. The organic phase was dried (Na2SO4), filtered and evaporated to dryness at rt to give 2-(4-methylcyclohex-3-enyl)propan-2-ol (2a) as a pale yellow oil (56.5 g; 85% yield). MS (EI), m/z 153 [M]+. 1H and 13C NMR spectra of 2a are identical to the described.10 This procedure was repeated for the five solvents tested (Table 2) and during dehydration yield optimization by variation of Amberlyst-15/alcohol 1a ratio (Fig. 1). | |
With pyridine; thionyl chloride; In dichloromethane; at -78℃; for 0.5h; | This experiment was performed under modified condition in the literature;11 to a stirred solution of alcohol 1n (1.0 g; 6.30 mmol; 1.0 equiv) in dry dichloromethane (20 mL) at rt was added dry pyridine (1.02 mL; 12.60 mmol; 2.0 equiv). After cooling to -78 C a solution of thionyl chloride (2.2 mL; 31.50 mmol; 5.0 equiv) in dry dichloromethane (10 mL) and dry pyridine (4 mL; 50.40 mmol; 8.0 equiv) was added dropwise. The reaction mixture was stirred for 30 min at the same temperature before quenching with saturated aqueous NaHCO3 (30 mL). The reaction mixture was allowed to warm to rt and the organic layer was separated. The aqueous phase was extracted with dichloromethane (5×50 mL). The combined organic layers were dried over MgSO4 by filtration to give a crude (pale yellow) oil. This residue was further purified by conventional column chromatography (eluent: from hexane to hexane/EtOAc (3:6)) to give (0.70 g; 79% overall yield) of a mixture of olefins 2n' (82%), 2n (7%) and 2n (11%), ratio determined by NMR; see NMR data of mixture in Supplementary data. | |
With Filtrol 20X acidic clay; at 135℃; | General procedure: To a 3 neck flask equipped with stirrer, thermocouple, and a glass spacer topped with a short path condenser was charged 168.53 g 2-butyl-1-octanol, and 4.03 g dried FILTROL 20× acidic clay catalyst. The mixture was heated to 160 C. with stirring and the pressure was reduced to 240 torr., and product was collected via distillation. Once distillation commenced the pressure was reduced to 160 torr over 20 minutes and the pot temperature fell to 135 C. After 2 h the system was cooled under vacuum. The two phase distillate was cooled causing the aqueous portion to freeze, i.e., placed in a commercial freezer overnight, and the organic portion was decanted. The aqueous phase was allowed to thaw and an additional 2 mL of organics were recovered and combined with the main organic portion to yield 88.28 g of a mixture of three C12 olefin isomers in roughly equal amounts, see table. Following the general procedure of Example 1, and adjusting the temperatures and pressures according to the volatility of the products, the alcohols of examples 2-6 were heated in the presence of FILTROL 20× acidic clay catalyst at the temperatures shown to produce a mixture of olefins V, Va and Vb. |