9-Bromononanoic acid

To a solution of concentrated nitric acid (10 mL, 258 mmol) 9-bromononanol (1 gr, 4.48 mmol) was added over a period of 30 minutes, maintaining a temperature of 25-30 To a solution of 9-Bromo- l-nonanol (1.50 g, 6.72 mmol) in acetone (27 ml) cooled at 0°C, a satured solution of NaHCOStep 1: Synthesis of 9-bromononanoic acid To a solution of 9-Bromo-l-nonanol (1.50 g, 6.72 mmol) in acetone (27 ml) cooled at 0°C, a saturated solution of NaHCOTo a stirred solution of 9-bromononanol (28.6 g, 128 mmol) in acetone (570 mL) was added dropwise 2-N Jones' reagent (420 mL) at 0 °C. The reaction mixture was stirred at rt for 10 min and then extracted with n-hexane (3×400 mL). The combined organic layers were washed with water and extracted with a saturated K2CO3 solution (3×400 mL). The combined aqueous layers were made acidic (pH l) with a 10percent H2SO4 solution and extracted with AcOEt. The organic layer was washed with water and brine and dried over MgSO4. After filtration, the solvent was evaporated in vacuo to give 9-bromononanoic acid (21 g, 71percent) as a colorless solid. Compound 3h was prepared from 1 and 9-bromononanoic acid in a manner similar to that described for compound 3a with a yield of 77percent as colorless needles (acetone/Et2O/n-hexane).Example 8 General procedure: In the oxygen atmosphere (oxygen balloon)Fe (NO3) 3 · 9H2O (40.4 mg, 0.10 mmol), 2, 2, 6, 6-tetramethylpiperidine nitrogen oxide (TEMPO, 15.5 mg, 0.10 mmol)KCl (7.5 mg, 0.10 mmol), Dodecanol (189.0 mg, 98% purity, 1.0 mmol) and1, 2-dichloroethane (DCE, 4 mL)Was added to a 50 mL Schlenk tube.Stir at room temperature for 12 h, TLC monitoring until completion of the reaction.The reaction solution was filtered through a short column of silica gel, eluted with ether (75 mL) and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1)The corresponding dodecanoic acid (199.2 mg, 100%) was obtained.

Molecular Weight:237.13
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:236.04119
Monoisotopic Mass:236.04119
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:115
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes