Acetic Acid → 4-Butylbenzene-1,2-diol

HRID 704002

Reaction equation

HRID 704002 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([O:13]C)[C:8]([O:11]C)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4].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])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 5921764-Butyl-1,2-dimethoxybenzene

Product 1

HCID 143688794-Butylbenzene-1,2-diolYield 80.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.64 g (29 mM) of 4-n-butylveratrole, 18.54 g (309 mM) of acetic acid and 55.62 g (323 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. The reaction mixture wa cooled to the room temperature and added with 50 ml of water. The separated oil was extracted with ether. The ether solution was successively washed with 50 ml of water, 75 g of 5% aqueous sodium thiosulfate solution, and further twice with each 50 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether, and vacuum distilled to obtain 3.89 g (23 mM) of 4-n-butylcatechol as light yellow liquid having a boiling point of 125° C./3 mmHg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. extractionThe separated oil was extracted with ether
  4. washThe ether solution was successively washed with 50 ml of water, 75 g of 5% 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-c703c937a7af42c4b4b326db16a54bd2
Source dataset
uspto-grants-1991_01
Patent number
US04985458

Linked notes

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