Hydrogen Peroxide → Tert-butyl 4-(2-hydroxyethyl)benzoate

HRID 742304Notes

Reaction equation

HRID 742304 reaction equation
C12BC(CCC1)CCC2.[CH:10]([C:12]1[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:14][CH:13]=1)=[CH2:11].[OH-:25].[Na+].OO>O1CCCC1.O>[OH:25][CH2:11][CH2:10][C:12]1[CH:24]=[CH:23][C:15]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 9990491t-Butyl 4-vinylbenzoate

Product 1

HCID 10331132Tert-butyl 4-(2-hydroxyethyl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9-borabicyclo[3.3.1]nonane (9-BBN, 5.65 g, 46.3 mmol) in anhydrous tetrahydrofuran was added to a solution of t-butyl 4-vinylbenzoate (8.47 g, 42.1 mmol) prepared in the Preparative Example 102 in anhydrous tetrahydrofuran in a nitrogen stream. The obtained mixture was stirred at room temperature for 3 hours. 15 ml of water and 17 ml of 3N NaOH were added to the reaction mixture successively, followed by the dropwise addition of 30% aqueous hydrogen peroxide at 50° C. or below. The obtained mixture was stirred as such for one hour and poured into water. The mixture thus obtained was extracted with ethyl acetate. The organic phase was washed with an aqueous solution of common salt, dehydrated and distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=1:1) to give the objective compound. yield: 8.71 g

Workup

  1. stirringThe obtained mixture was stirred as such for one hour
  2. customThe mixture thus obtained
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase was washed with an aqueous solution of common salt
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe obtained residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=1:1)
  8. customto give the objective compound

Sources & evidence

ORD record
ord-50525da14e664001ad17e0bcd5a6a53b
Source dataset
uspto-grants-1996_09
Patent number
US05554615

Reaction notes

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