ChemicalBook CAS DataBase List 5-Heptylresorcinol

5-Heptylresorcinol synthesis

13synthesis methods

Product Name:5-Heptylresorcinol
CAS Number:500-67-4
Molecular formula:C13H20O2
Molecular Weight:208.3

To a solution of 1-heptyl-3,5-dimethoxy-Benzene (388 mg, 1.41 mmol) in dry CH2Cl2 (47 mL) at -78 °C under an argon atmosphere was added boron tribromide (3.4 mL, 1 M solution in CH2Cl2). Following this addition, the reaction temperature was gradually raised over a period of 3 h to 0 °C, and the stirring continued at that temperature until the reaction was completed (28 h). Unreacted boron tribromide was destroyed by adding methanol at -78 °C. The resulting mixture was warmed at room temperature and stirred for 40 min, and the volatiles were removed in vacuo. The residue was diluted with EtOAc and washed with saturated NaHCO3 solution, water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (45% diethyl etherpetroleum ether) afforded 340 mg (97% yield) of the compound as a slightly brown viscous oil: 5-Heptylresorcinol (. The synthesis was carried out as described for 5-Heptylresorcinol by using 15 (1.18 g, 5 mmol) and boron tribromide (11 mL, 11 mmol, 1 M solution in CH2Cl2) in anhydrous CH2Cl2 (40 mL): yield 91% (0.95 g); slightly brown solid; mp 53-54 °C (lit.63 mp 55-56 °C); spectral and analytical data were reported previously.
5-Heptylresorcinol synthesis

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500-67-4
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Yield:500-67-4 96%

Reaction Conditions:

with hydrogen bromide;acetic acid in water at 125; for 3 h;Inert atmosphere;

Steps:

5-propylbenzene-1,3-diol (19a).

General procedure: In a 100 mL round bottom flask, open to the atmosphere was added the crude product SI-2 (0.736 g, 4.08 mmol, 1.0 equiv.) and a 1:1 mixture of glacial acetic acid (20 mL, 349.7 mmol, 17.4 M) and hydrobromic acid (48% in H2O, 20 mL, 368.3 mmol, 18.4 M). The reaction mixture was refluxed at 125 °C for 3 hours while stirring, or until the starting material was consumed via TLC analysis. At this point, the reaction was allowed to cool to room temperature and quenched by the addition of DI H2O. The biphasic solution was added to a separatory funnel, wherein the organic portion was extracted Et2O (ca. 3x 20 mL). The organic layers were then combined, neutralized with a concentrated sodium bicarbonate solution (ca. 30 mL), washed with a saturated brine solution (ca. 50 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford the final product without purification (0.609 g, 99% yield) as a pale yellow oil.

References:

Golliher, Alexandra E.;Tenorio, Antonio J.;Dimauro, Nina O.;Mairata, Nicolas R.;Holguin, F. Omar;Maio, William [Tetrahedron Letters,2021,vol. 67] Location in patent:supporting information