Pyrogallol → 3-Allyloxycatechol

HRID 1614719Notes

Reaction equation

HRID 1614719 reaction equation
[C:1]1([CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:3]=1[OH:4])[OH:2].[H-].[Na+].B(OCC)(OCC)OCC.B([O-])([O-])O[CH2:24][CH:25]=[CH2:26]>CN(C)C=O>[CH2:26]([O:2][C:1]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:3]=1[OH:4])[CH:25]=[CH2:24]

Participants

6

Reactant 4

HCID 1057PyrogallolHCID 9009Triethyl borateHCID 24758Sodium hydrideHCID 86746676Dioxido(prop-2-enoxy)borane

Product 1

HCID 122088813-Allyloxycatechol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3.8 g of pyrogallol, 76 ml of anhydrous dimethylformamide and 2.72 g of sodium hydride in suspension at 53% in oil was stirred for 3 hours under an inert gas atmosphere and then 5.27 ml of triethyl borate were added, followed by stirring for 30 minutes. Then, 2.6 ml of allyl borate in solution in 26 ml of dimethylformamide were added over 45 minutes and the mixture was stirred for 16 hours and poured into water-ice-N hydroohloric acid mixture. Extraction took place with ethyl acetate and the crude product was chromatographed on silica, eluting with a cyclohexane-ethyl acetate mixture (7-3) to obtain 3.8 g of the expected product in the form of white crystals (Yield: 76.3%).

Workup

  1. stirringby stirring for 30 minutes
  2. stirringthe mixture was stirred for 16 hours
  3. extractionExtraction
  4. customthe crude product was chromatographed on silica
  5. washeluting with a cyclohexane-ethyl acetate mixture (7-3)

Sources & evidence

ORD record
ord-81c056a39cf342d281403ba0beb904ef
Source dataset
uspto-grants-1993_03
Patent number
US05198571

Reaction notes

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