Reaction #833543

Reaction equation

16-bromohexadecanoic acid

→

desired product

Yield 93.2%

16-Bromohexadecan-l-ol

Yield 93.2%

Solvents

THF

THF

Conditions

Workup

1. 1
   OtherReaction mixture
2. 2
   Otheradditional 1 hr
3. 3
   Otherat RT
4. 4
   workup.ADDITIONAfter that time the resulted mixture was poured
5. 5
   workup.STIRRINGwith stirring, into a vessel
6. 6
   ExtractionOrganic compounds were extracted with 3×200 ml of ether
7. 7
   Dryingdried over sodium sulfate
8. 8
   OtherAfter removal of ether material
9. 9
   workup.DISSOLUTIONwas dissolved in minimum amount of dichloromethane
10. 10
    Otherpurified by silica gel chromatography (100% dichloromethane as eluent)

Procedure

Under inert atmosphere 10 ml of BH3 THF complex (1.0 M THF solution) were added to 30 ml THF solution of 2.15 gr (6.41 mmole) of 16-bromohexadecanoic acid at −20° C. Reaction mixture was stirred at this temperature for 2 hrs and then additional 1 hr at RT. After that time the resulted mixture was poured, with stirring, into a vessel containing 200 ml of ice/saturated sodium bicarbonate aqueous solution. Organic compounds were extracted with 3×200 ml of ether. The ether fractions were combined and dried over sodium sulfate. After removal of ether material was dissolved in minimum amount of dichloromethane and purified by silica gel chromatography (100% dichloromethane as eluent). 1.92 gr (93% yield) of the desired product were obtained.

Source