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

HRID 864516Notes

Reaction equation

HRID 864516 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 mmoles) and solid pyridine hydrochloride (150 g, 1.30 mole) was warmed to 180° C. After 7.5 hours the reaction was cooled to 110° C. and 50 ml of water was added slowly. After the reaction cooled to room temperature, it was diluted with 100 ml of water and extracted several times with ethyl acetate. The ethyl acetate extract was washed once with 2N hydrochloric acid and then dried over magnesium sulfate. Filtration and solvent removal gave 38.5 g of an orange solid. The title product was purified by recrystallization from dichloromethane providing 11.86 g (41%) of yellow crystals.

Workup

  1. temperatureAfter 7.5 hours the reaction was cooled to 110° C.
  2. temperatureAfter the reaction cooled to room temperature
  3. extractionextracted several times with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed once with 2N hydrochloric acid
  6. dry with materialdried over magnesium sulfate
  7. filtrationFiltration and solvent removal

Sources & evidence

ORD record
ord-9e5445ece71347f0a2f6f59922223507
Source dataset
uspto-grants-1996_10
Patent number
US05563164

Reaction notes

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