Hydrogen Bromide → 16-Bromo-1-hexadecanol

HRID 1289392Notes

Reaction equation

HRID 1289392 reaction equation
[CH2:1](O)[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][OH:17].[BrH:19].C1(C)C=CC=CC=1>O>[Br:19][CH2:1][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][OH:17]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1140TolueneHCID 821841,16-Hexadecanediol

Product 1

HCID 275701316-Bromo-1-hexadecanolYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 10 g of 1,16-hexadecanediol, 26 g of 48% hydrobromic acid, and 400 ml of toluene were placed in a 1 L flask. The reaction mixture was stirred under reflux for 48 hours while water in the system was removed. The reaction mixture was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1) and recrystallized from hexane to obtain 5.7 g of 16-bromo-1-hexadecanol (Y: 46%). The compound thus obtained had a purity of 95% by GC.

Workup

  1. customwas removed
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1)
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-bd9d9f9ef46749bcbbf9dc5bf3f18b57
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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