Acetic Acid → HCID 53989296, compound

HRID 346256Notes

Reaction equation

HRID 346256 reaction equation
[BrH:1].[CH:2]([CH:5]([CH2:8][OH:9])[CH2:6]O)([CH3:4])[CH3:3].[C:10]([OH:13])(=O)[CH3:11]>>[C:10]([O:9][CH2:8][CH:5]([CH2:6][Br:1])[CH:2]([CH3:3])[CH3:4])(=[O:13])[CH3:11]

Participants

4

Reactant 3

HCID 176Acetic Acid3×HCID 260Hydrogen Bromide2×HCID 2007341,3-Propanediol, 2-isopropyl-

Product 1

HCID 53989296HCID 53989296, compound

Procedure

A solution of hydrobromic acid in acetic acid (30%, 0.5 ml) was added to a solution of 2-isopropylpropane-1,3-diol (10 g) in glacial acetic acid (20 ml) and the mixture heated to reflux for 20 minutes. A further portion of 30% hydrobromic acid in acetic acid (26 ml) was then added dropwise and the resulting mixture maintained at reflux for a further 6 hours. The solvent was then removed in vacuo, and residues removed by azeotroping with hexane, to leave 2-bromomethyl-3-methylbutyl acetate (15 g) which was used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 20 minutes
  3. temperaturethe resulting mixture maintained
  4. temperatureat reflux for a further 6 hours
  5. customThe solvent was then removed in vacuo, and residues
  6. customremoved
  7. customby azeotroping with hexane

Sources & evidence

ORD record
ord-6a4eb08951934dae86375171c7c08173
Source dataset
uspto-grants-1991_10
Patent number
US05061726

Reaction notes

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