Hydrogen Peroxide → Methyl 2-benzyloxy-5-(2-hydroxyethyl)benzoate

HRID 1862617Notes

Reaction equation

HRID 1862617 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH:19]=[CH2:20])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12BC(CCC1)CCC2.[OH-:30].[Na+].OO>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][OH:30])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 18620104HCID 18620104, compound

Product 1

HCID 18620142Methyl 2-benzyloxy-5-(2-hydroxyethyl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the obtained methyl 2-benzyloxy-5-vinylbenzoate (1.52 g) in tetrahydrofuran (15 ml) was added dropwise a solution of 9-borabicyclo[3.3.1]nonane (726 mg) in tetrahydrofuran (15 ml) at −20° C., and the mixture was stirred for 17.5 hours at room temperature. After the reaction mixture was cooled to 0° C., 2N aqueous sodium hydroxide solution (8.5 ml) and 30% aqueous hydrogen peroxide solution (6.8 ml) were added to the mixture, and the resulting mixture was stirred for 3 hours at room temperature. To the reaction mixture was added water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=3/2) gave methyl 2-benzyloxy-5-(2-hydroxyethyl)benzoate (1.30 g).

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. stirringthe resulting mixture was stirred for 3 hours at room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-5f4a70927e91450ea66a1d1964a9dce0
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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