Acetic Acid → 4-(2-Methylpropyl)-1,2-benzenediol

HRID 1029702Notes

Reaction equation

HRID 1029702 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([O:13]C)[C:8]([O:11]C)=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3].C(O)(=O)C.Br>O>[CH2:1]([C:5]1[CH:6]=[C:7]([OH:13])[C:8](=[CH:9][CH:10]=1)[OH:11])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 14372664HCID 14372664, compound

Product 1

HCID 143726654-(2-Methylpropyl)-1,2-benzenediolYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50.83 g (262 mM) of 4-isobutylveratrole, 167.82 g (2.795 mM) of acetic acid and 502.18 g (2.917 mM) of 47% hydrobromic acid was heated under reflux for 19 hours with stirring. The reaction mixture was cooled to the room temperature and added with 400 ml of water. The separated oil was extracted with ether. The ether solution was successively washed with 400 ml of water, 660 g of aqueous sodium thiosulfate solution, and further twice with each 400 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 35.68 g (215 mM) of 4-iso-butylcatechol as yellow viscous liquid having a boiling point of 117°-120° C./2 mmHg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. extractionThe separated oil was extracted with ether
  4. washThe ether solution was successively washed with 400 ml of water, 660 g of aqueous sodium thiosulfate solution
  5. dry with materialThe resulting solution was dried with anhydrous sodium sulfate
  6. distillationdistilled off ether, and vacuum
  7. distillationdistilled

Sources & evidence

ORD record
ord-9498a04803fb4703bc2941601517816a
Source dataset
uspto-grants-1992_04
Patent number
US05102906

Reaction notes

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