16-Bromohexadecanoicacid

Synthesis of 16-Bromohexadecanoic Acid 2 10.62 g (0.039 mol) of 16-hydroxyhexadecanoic acid were placed in a three-necked flask under nitrogen, equipped with a condenser, a mechanical stirrer anda nitrogen inlet, followed by addition of 50 ml of hydrobromic acid at 33percent byweight in acetic acid and 18.6 ml of concentrated sulfuric acid.The assembly was then connected to three traps containing sodium hydroxide, aqueous sodium hydroxide at 25percent by weight and saturated potassium carbonate solution. The reaction mixture was stirred vigorously for 15 hours at 2000 and then refluxed for 3 hours. After cooling, the reaction mixture was poured into ice-water and the precipitate formed was extracted with dichloromethane (3 x 100 ml). The organic phase was washed with distilled water (3x50 ml), dried over MgSO4 and evaporated under vacuum. 11 g of 16-bromohexadecanoic acid Br-C15H30- C(O)OH were recovered in the form of an off-white solid.1 H NMR and mass spectra compliant.6.9. Example 10J)-erythro-2-N~ (16r-Bromohexadecanoyl)-sphingosine (2j). [00307] (A). Synthesis of 16-bromohexadecanoyl chloride. 16-Bromohexadecanoic acid (97%, 1.9 g, 5.7 mmol) was dissolved in dry cyclohexane (30 mL) by stirring at 450C for 30 min. To this well-stirred and water-cooled mixture one drop (-0.02 mL) of dry pyridine was added following oxalyl chloride (99%, 0.75 mL, 8.6 mmol) over 1 min. After the addition was completed, the cooling bath was removed and the reaction mixture was heated at 50C for 15 min and then left to reach room temperature for an additional 30 min. The reaction mixture was evaporated to dryness by purging dry nitrogen gas into the reaction flask following drying the residue under vacuum (~1 torr) at +4C over 30 min. The freshly prepared acid chloride was dissolved in dry THF and taken directly to the next reaction.9.4 g (0.028 mol) of (1) Under ice bath conditions, 5 to 15 mL of thionyl chloride (SOCl2) was slowly added dropwise to 5 to 15 mmol of 16-bromohexaic acid.After the addition is completed, Continue to stir for 5 to 10 minutes, Then heat up to 60 ~ 90 C, Reaction for 6 hours, Producing the product 16-bromohexadecanoyl chloride, The reaction is over, Removal of excess thionyl chloride (SOCl2);5.4 g of bromohexadecanoic acid and 20 mL of thionyl chloride were placed in a round bottom flask and reacted at 80 C for 2 hours.The mixed solution is concentrated in a vacuum to obtain of bromohexadecanoyl chloride;a. Synthesis of

Molecular Weight:335.32
XLogP3:6.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:15
Exact Mass:334.15074
Monoisotopic Mass:334.15074
Topological Polar Surface Area:37.3
Heavy Atom Count:19
Complexity:195
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes