Hydrogen Bromide → 12-Bromo-1-dodecanol

HRID 2204026Notes

Reaction equation

HRID 2204026 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][OH:13].[BrH:15].O>C1(C)C=CC=CC=1>[Br:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 797581,12-Dodecanediol

Product 1

HCID 13789512-Bromo-1-dodecanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of dodecane-1,12-diol (8.365 g, 42.75 mmol), 48% HBr in water (9.7 ml, 85.50 mmol) and toluene (120 ml) were added and the reaction mixture refluxed for 3 h. The reaction mixture was then concentrated, the crude compound was dissolved in DCM (150 ml), washed with water, NaHCO3 brine solution, dried over MgSO4 and concentrated. The crude product was purified by silica gel column (5% EtOAc in hexane) to obtain 12-bromododecan-1-ol as an off-white low melting solid (8.87 g, 78%).

Workup

  1. temperaturethe reaction mixture refluxed for 3 h
  2. concentrationThe reaction mixture was then concentrated
  3. dissolutionthe crude compound was dissolved in DCM (150 ml)
  4. washwashed with water, NaHCO3 brine solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column (5% EtOAc in hexane)

Sources & evidence

ORD record
ord-78bf3ca46c3b41118ec7f26232d36585
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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