Boron tribromide → 1,3-Benzenediol, propyl-

HRID 893461Notes

Reaction equation

HRID 893461 reaction equation
C[O:2][C:3]1[C:8]([CH2:9][CH2:10][CH3:11])=[C:7]([O:12]C)[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:8]([CH2:9][CH2:10][CH3:11])=[C:7]([OH:12])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 5248571,3-Dimethoxy-2-propylbenzene

Product 1

HCID 2620601,3-Benzenediol, propyl-Yield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

2,4,-Dimethoxy-3-propylbenzene (7.2 g, 39.94 mmol) was dissolved in 50 ml methylene chloride and the solution was cooled to -70° C. then 87.0 ml of 1 M boron tribromide in methylene chloride was added over a period of 1 hour. The reaction mixture was stirred at -70° C. for 1 hour, then at room temperature for 2 hours. The reaction mixture was poured into 250 ml of ice water very slowly. This mixture was extracted 3 times with 100 ml methylene chloride. The extracts were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under vacuum to give the product as a white solid (4.9 g, 81.7%).

Workup

  1. waitat room temperature for 2 hours
  2. extractionThis mixture was extracted 3 times with 100 ml methylene chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-961915064cca4e26887de298a775b3a0
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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