Water → 3-(4-Bromophenyl)propane-1,2-diol

HRID 866908Notes

Reaction equation

HRID 866908 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]2[CH2:11][O:10]2)=[CH:4][CH:3]=1.C(O)(=O)C(O)=[O:14].O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([OH:14])[CH2:11][OH:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 971Oxalic AcidHCID 116800982-[(4-bromophenyl)methyl]oxirane

Product 1

HCID 203327403-(4-Bromophenyl)propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 90 parts of 2-(4-bromophenylmethyl)oxirane, 8 parts of ethanedioic acid, 100 parts of water and 300 parts of 1,4-dioxane is stirred and refluxed overnight. The reaction mixture is evaporated. The residue is dissolved in trichloromethane. The solution is washed with 110 parts of a sodium hydroxide solution 10%, dried, filtered and evaporated. This The is distilled (bp. 165° C at 0.6 mm. pressure). The distillate is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding 25 parts of 3-(4-bromophenyl)-1,2-propanediol; mp. 60.6° C.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture is evaporated
  3. dissolutionThe residue is dissolved in trichloromethane
  4. washThe solution is washed with 110 parts of a sodium hydroxide solution 10%
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThis The is distilled (bp. 165° C at 0.6 mm. pressure)
  9. customThe distillate is crystallized from 2,2'-oxybispropane
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-a32991b8965b496f9fee34f42b4e9042
Source dataset
uspto-grants-1978_07
Patent number
US04101666

Reaction notes

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