Hydrogen Bromide → 5-Ethylbenzene-1,3-diol

HRID 1003950Notes

Reaction equation

HRID 1003950 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([O:11]C)[CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([OH:11])[CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 524877Benzene, 1,3-dimethoxy-5-ethyl

Product 1

HCID 127958985-Ethylbenzene-1,3-diolYield 92.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,3-Dimethoxy-5-ethylbenzene (7.69 g) is dissolved in acetic acid (80 ml), and thereto is added with stirring 47% hydrobromic acid at room temperature. The mixture is refluxed for three hours, and the reaction mixture is cooled to room temperature. The mixture is concentrated to dryness under reduced pressure, and the residue is dissolved in ethyl acetate. The organic layer is washed successively with water and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure. The residue is recrystallized from diisopropyl ether-hexane to give 1,3-dihydroxy-5-ethylbenzene (5.94 g), m.p. 97-98° C.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed for three hours
  3. concentrationThe mixture is concentrated to dryness under reduced pressure
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. washThe organic layer is washed successively with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-d254cc20ae57415d9e2941cf46b040f9
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Reaction notes

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