Hydrogen Peroxide → HCID 178520942, compound

HRID 1404401Notes

Reaction equation

HRID 1404401 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.[OH-:18].[Na+].OO>C1COCC1>[CH2:11]([O:10][CH2:9][CH2:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([CH2:1][OH:18])[CH2:3][CH2:4]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86723000HCID 86723000, compound

Product 1

HCID 178520942HCID 178520942, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0 C) solution of ((2-(4-methylenecyclohexyl)ethoxy)methyl)benzene (9.68 g, 41.66 mmol) in THF (200 mL) was added B2H6Me2S complex (2M in THF, 41.66 mL, 83.32 mmol) under N2. After being stirred at 0° C. for 2 h and at rt for another 2 h, the solution was cooled to 0° C. and added a mixture of 3M aqueous NaOH solution (34 ml) and 30% hydrogen peroxide solution (34 mL) dropwise. The resulting mixture was stirred at 0° C. for 1 h and at rt for 1.5 h. Aqueous workup and purification by flash column chromatography (eluent: 40% EtOAc in hexanes) gave the product as yellow oil (7.04 g, 68%). LC/MC: 249.1 (MH)

Workup

  1. temperaturethe solution was cooled to 0° C.
  2. additionadded
  3. stirringThe resulting mixture was stirred at 0° C. for 1 h and at rt for 1.5 h
  4. customAqueous workup and purification by flash column chromatography (eluent: 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7a0c37f5c20d44d9a3ac18337c599e9a
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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