Benzyl Bromide → 4-(Benzyloxy)-1,2-benzenediol

HRID 1614723Notes

Reaction equation

HRID 1614723 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[OH:9].[H-].[Na+].B(OCC)(OCC)OCC.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[CH2:22]([O:8][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([OH:9])[CH:4]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 9009Triethyl borateHCID 107871,2,4-BenzenetriolHCID 24758Sodium hydride

Product 1

HCID 155069714-(Benzyloxy)-1,2-benzenediolYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.37 g of 1,2,4-trihydroxy benzene and 30 ml of anhydrous dimethylformamide were mixed together under an inert gas atmosphere and then 0.984 g of sodium hydride in suspension at 53% in oil was added at 15°-20° C. The mixture was stirred for one hour and 1.906 ml of triethyl borate were added. The mixture was stirred for one hour, and 1.29 ml of benzyl bromide in solution in 20 ml of dimethylformamide were added over 2 hours. The mixture was stirred for 16 hours at ambient temperature and then was poured into a water-ice-N hydrochloric acid mixture. Extraction took place with ethyl acetate followed by evaporation to dryness. The residue was washed with petroleum ether, and chromatographed on silica eluting with a cyclohexane-ethyl acetate (6-4) mixture to obtain 1.36 g of the crystallized expected product (Yield: 58%).

Workup

  1. stirringThe mixture was stirred for one hour
  2. stirringThe mixture was stirred for 16 hours at ambient temperature
  3. extractionExtraction
  4. customfollowed by evaporation to dryness
  5. washThe residue was washed with petroleum ether
  6. customchromatographed on silica eluting with a cyclohexane-ethyl acetate (6-4) mixture
  7. customto obtain 1.36 g of the

Sources & evidence

ORD record
ord-9fd5685655574b3aaa8630db1cb685b6
Source dataset
uspto-grants-1993_03
Patent number
US05198571

Reaction notes

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