9-Bromononanol

solid

In a 500 mL round bottom flask fitted with a Dean-Stark apparatus 1 , 9-nonanediol (Sigma- Aldrich) (20 g, 0.125 mol) was dissolved in toluene (500 ml). To this solution was added 21 mL hydrobromic acid (48 percent, 188 mmol) and the mixture was heated for 30 h at reflux. The water formed during the reaction was removed using a Dean—Stark trap. The progress of the reaction monitored by thin layer chromatography (TLC) indicated that all starting materials reacted withHBr. After cooling to room temperature, the mixture was washed with 1 M HCI (100 mL), 1M NaOH (100 ml), 100 mL water and finally with 100 mL brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude oil obtained was fractionally distilled to give 9-bromononanol in 94 percent yield. B.p.:124-128 ° C/2 mmHg (lit: 125- 126 °C/2 mmHg).General procedure: To a stirred solution of 1, 6-hexanodiol 1a (1.00 equiv.), 1, 9-nonanediol 1b (1.00 equiv.), or 1, 12-dodecanediol 1c (1.00 equiv.), in 30 mL of toluene was added HBr 48 percent (2.00 equiv.). The reaction was stirred at 110 °C for 24 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography over silica gel, eluting with hexane/EtOAc 9:1, to yield pure haloalcohol 2a–c. These compounds were transformed into their corresponding azido alcohols 3a–c by SNAccording to a known protocol, 1, 9-nonanediol (1 kg) was added to toluene (20 L), hydrobromic acid (40percent, 2.5 L) was added with stirring, heated to reflux (Internal temperature 90-100 ° C) 24 hrs. (4 L) and cold water (4 L) were added and the layers were stirred. The organic phase was washed successively with saturated aqueous sodium bicarbonate and aqueous solution, dried over anhydrous sodium sulfate, dried over anhydrous sodium bicarbonate, Spin dry 1.6 kg crude product, adding n-hexane 4.8 L, stirring and heating dissolved, Crystallization was carried out to give 1.1 kg of 9-bromo-1-nonanol.1. Add 1, 9-nonanediol (1 kg) to toluene (20 L). Add hydrobromic acid (40percent, 2.5 L) with stirring and heat to reflux (internal temperature 90-100 ° C) for 24 hrs. The heating was stopped and cooled to 40 ° C. Ethyl acetate (4L) and cold water (4L) were added. The mixture was stirred and layered. The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and spun dry to 1.6 kg The crude product was added with 4.8 L of n-hexane, stirred and heated to dissolve and crystallized by cooling to obtain 1.1 kg of 9-bromo-1-nonanol1, 9-Nonanediol (1 kg) was added to toluene (20 L) and hydrobromic acid (40percent, 2.5 L)Heat reflux (internal temperature 90-100 ) 24 hrs. Stop heating, cooled to 40 , Ethyl acetate (4L) and cold water (4L) were added, the mixture was stirred and layered, The organic phase was washed successively with saturated aqueous sodium bicarbonate solution and aqueous solution, dried over anhydrous sodium sulfate, Spin dried to 1.6 kg of crude product, adding n-hexane 4.8 L, stirring heated to dissolve, cooling crystallization, 1.1 kg of 9-bromo-1-nonanol were obtained

Molecular Weight:223.15
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:8
Exact Mass:222.06193
Monoisotopic Mass:222.06193
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:66.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes