Hydrogen Peroxide → HCID 21288128, compound

HRID 868284Notes

Reaction equation

HRID 868284 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[O:11][CH2:12][O:13][CH3:14])=[CH2:2].B.[O:16]1CCCC1.[OH-].[Na+].OO>O1CCCC1>[OH:16][CH2:2][CH2:1][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[O:11][CH2:12][O:13][CH3:14]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 21288122HCID 21288122, compound

Product 1

HCID 21288128HCID 21288128, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 33.8 g (0.174 moles) of 2-ethenyl-4-methoxy-1-O-methoxymethylphenol in 300 ml of dry tetrahydrofuran at 0° was added 120 ml of a 1.0M borane-tetrahydrofuran solution. The solution was stirred at room temperature for 60 minutes, cooled to 0° and 48 ml of 10% NaOH was added dropwise. Then 41 ml of 30% H2O2 was added with caution and the mixture was stirred at room temperature for 30 minutes. The solution was partitioned between ether and water and the ether layer was washed with aqueous NaHCO3 and brine, dried (Na2SO4) and evaporated. The oily residue was purified by Prep. 500 HPLC using 40% ethylacetatehexane to afford 27.3 g (73%) of 2-(2-hydroxyethyl)-4-methoxy-1-O-methoxymethylphenol as a colorless liquid. NMR (CDCl3) δ2.15 (s, br, 1H, --OH), 2.8 (t, 2 H, J=7 Hz), 3.40 (s, 3H), 3.65 (s, 3H), 3.73 (m, 2H), 5.05 (s, 2H), 6.55 (d of d, 1H), 6.61 (s, 1H), 6.88 (d, 1H).

Workup

  1. temperaturecooled to 0°
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. customThe solution was partitioned between ether and water
  4. washthe ether layer was washed with aqueous NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe oily residue was purified by Prep

Sources & evidence

ORD record
ord-bfb8c17db0314668babb830bddb68abd
Source dataset
uspto-grants-1988_10
Patent number
US04778818

Reaction notes

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