16-Bromohexadecanoic acid → 16-Bromo-1-hexadecanol

HRID 324930Notes

Reaction equation

HRID 324930 reaction equation
B.C1COCC1.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24]>C1COCC1>[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24]

Participants

4

Reactant 2

HCID 62039716-Bromohexadecanoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 275701316-Bromo-1-hexadecanolYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 dicloromethane and purified by silica gel chromatography (100% dicloromethane as eluent). 1.92 gr (93% yield) of the desired product were obtained.

Workup

  1. customReaction mixture
  2. customadditional 1 hr
  3. customat RT
  4. additionAfter that time the resulted mixture was poured
  5. stirringwith stirring, into a vessel
  6. extractionOrganic compounds were extracted with 3×200 ml of ether
  7. dry with materialdried over sodium sulfate
  8. customAfter removal of ether material
  9. dissolutionwas dissolved in minimum amount of dicloromethane
  10. custompurified by silica gel chromatography (100% dicloromethane as eluent)

Sources & evidence

ORD record
ord-b671a2f87bca4771be3408b5cd15b2d1
Source dataset
uspto-grants-2001_04
Patent number
US06221583B1

Reaction notes

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