1,3-Dimethoxy-2-propylbenzene → 1,3-Benzenediol, propyl-

HRID 741767Notes

Reaction equation

HRID 741767 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[C:4]=1[CH2:11][CH2:12][CH3:13].Cl.N1C=CC=CC=1>O>[CH2:11]([C:4]1[C:5]([OH:9])=[CH:6][CH:7]=[CH:8][C:3]=1[OH:2])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 5248571,3-Dimethoxy-2-propylbenzeneHCID 10176127Pyridinium chloride

Product 1

HCID 2620601,3-Benzenediol, propyl-Yield 133.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
180 °C

Procedure

A mixture of solid 1,3-dimethoxy-2-propylbenzene (33.70 g, 190 mmol) and solid pyridine hyrochloride (150 g, 1.30 mol) were warmed to 180° C. After 7.5 hours, the reaction was cooled to 110° C. and 50 mL of H2O was added slowly. After the reaction cooled to room temperature, it was diluted with 100 mL of water and extracted several times with EtOAc. The EtOAc extract was washed once with 2N HCl and then dried over MgSO4. Filtration and solvent removal gave 38.5 g of an orange solid. The product was purified by recrystallization from dichloromethane providing 11.86 g (41%) of yellow crystals.

Workup

  1. temperaturethe reaction was cooled to 110° C.
  2. temperatureAfter the reaction cooled to room temperature
  3. extractionextracted several times with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed once with 2N HCl
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-a945d7cbd49945a89912187eec72c4aa
Source dataset
uspto-grants-1996_09
Patent number
US05552441

Reaction notes

Loading…