Hydrogen Peroxide → 2,4-Dibenzyloxyphenol

HRID 322862Notes

Reaction equation

HRID 322862 reaction equation
C([O:8][C:9]1[C:10]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([CH:14]=[CH:15][CH:16]=1)C=O)C1C=CC=CC=1.OO.S([O-])([O-])=O.[Na+].[Na+]>S(=O)(=O)(O)O.CO>[CH2:18]([O:17][C:10]1[CH:11]=[C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:16][C:9]=1[OH:8])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 10870855Dibenzyloxybenzaldehyde

Product 1

HCID 106383482,4-DibenzyloxyphenolYield 41.6%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

Concentrated sulphuric acid (2-3 drops) is added to a stirred solution of dibenzyloxybenzaldehyde (1.5 g) in methanol (50 mL), resulting in a thick precipitate. The mixture is stirred for 5 minutes then hydrogen peroxide (1 g; 27.5% in water) is added in one portion and stirring is continued for 2 hours. The resulting brown solution is treated with 10% aqueous sodium sulphite solution (10 mL) then evaporated to low bulk. The residue is treated with water (50 mL), the solid washed with water, dried and crystallised from cyclohexane, with charcoal treatment, to give 2,4-dibenzyloxyphenol (0.3 g) as a white powder, m.p. 82-83° C. [Elemental analysis:- C,78.2; H,5.79%. Calculated:- C,78.4; H,5.92%].

Workup

  1. customresulting in a thick precipitate
  2. stirringstirring
  3. waitis continued for 2 hours
  4. customthen evaporated to low bulk
  5. additionThe residue is treated with water (50 mL)
  6. washthe solid washed with water
  7. customdried
  8. customcrystallised from cyclohexane, with charcoal treatment

Sources & evidence

ORD record
ord-fe40040671c04339b28dd52e0ac87024
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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