Hydrogen Bromide → 1-Octanol, 8-bromo-

HRID 1769014Notes

Reaction equation

HRID 1769014 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[BrH:11]>C1C=CC=CC=1>[Br:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 694201,8-Octanediol

Product 1

HCID 1626071-Octanol, 8-bromo-Yield 71%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1,8-Octanediol (14.62 g, 0.1 mole) was dissolved in benzene (200 mls) and 12.5 mls of conc (46.48%) aqueous HBr added. The mixture was then heated overnight at reflux whilst removing the water using a Dean & Stark apparatus. About 12 mls of water were rapidly removed within the first 4 hours. The crude mixture was washed with 6N NaOH (100 mls), 10% aq HCl (100 mls), water (2×200 mls) and brine (150 mls). The solvent was removed to give a colourless liquid, (14.8 g, 71%) 1-bromooctan-8-ol.

Workup

  1. temperatureThe mixture was then heated overnight
  2. temperatureat reflux
  3. customwhilst removing the water using a Dean & Stark apparatus
  4. customAbout 12 mls of water were rapidly removed within the first 4 hours
  5. washThe crude mixture was washed with 6N NaOH (100 mls), 10% aq HCl (100 mls), water (2×200 mls) and brine (150 mls)
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-6fd09eaea7654231beec09d9bf3b033e
Source dataset
uspto-grants-1995_01
Patent number
US05380732

Reaction notes

Loading…