ChemicalBook CAS DataBase List 5-butylbenzene-1,3-diol

5-butylbenzene-1,3-diol synthesis

10synthesis methods

Product Name:5-butylbenzene-1,3-diol
CAS Number:46113-76-2
Molecular formula:C10H14O2
Molecular Weight:166.22

51768-57-1
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46113-76-2
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Yield:46113-76-2 78%

Reaction Conditions:

with boron tribromide in dichloromethane at 0 - 20;

Steps:

1.8

[0089] Step 8. To a solution of l-butyl-3,5-dimethoxybenzene (7.5 g, 38.6 mmol) in dichloromethane (75 mL) was added drop-wise BBr₃ (24.2 g, 96.6 mol) at 0 °C. The reaction mixture was stirred at room temperature overnight. The mixture was quenched with H₂0 and neutralized with NaHC0₃. Dichloromethane (100 mL) was added and the organic layer was washed with water (2x50 mL), dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column (eluting with 5: 1 petroleum ether/ethyl acetate) to give 5- butylbenzene-l,3-diol (5 g, 78%). 1H NMR (400 MHz, CDC1₃) δ: 0.91 (t, 3H), 1.33 (m, 2H), 1.57 (m, 2H), 2.49 (t, 2H), 4.64 (s, 2H), 6.17 (s, 1H), 6.24 (s, 2H).

References:

WO2013/148365,2013,A1 Location in patent:Page/Page column 0089