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

HRID 131073Notes

Reaction equation

HRID 131073 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18]>C1COCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18]

Participants

3

Reactant 1

HCID 62039716-Bromohexadecanoic acid

Product 1

HCID 275701316-Bromo-1-hexadecanolYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under inert atmosphere 10 ml of BH3OTHF 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.

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 dichloromethane
  10. custompurified by silica gel chromatography (100% dichloromethane as eluent)

Sources & evidence

ORD record
ord-fba9a2ce91414060b04b059dcac62269
Source dataset
uspto-grants-2008_06
Patent number
US07384749B2

Reaction notes

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