Hydrogen Peroxide → HCID 15617919, compound

HRID 1762658Notes

Reaction equation

HRID 1762658 reaction equation
B.CC(=CC)C.[CH2:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:8]=[CH2:9].[OH-:28].[Na+].OO>O1CCCC1.O>[OH:28][CH2:9][CH2:8][CH2:7][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 105532-Methyl-2-buteneHCID 14798Sodium HydroxideHCID 13119971HCID 13119971, compound

Product 1

HCID 15617919HCID 15617919, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane (1.0M in tetrahydrofuran; 100 mL, 0.100 mole) was treated at 0° with a solution of 2-methyl-2-butene (2.0M in tetrahydrofuran; 100 mL, 0.200 mole) over 40 minutes, and the resulting solution stirred at 0° for 2 hours. A solution of 2-(2-propenyl)-1-benzyloxynaphthalene (27.40 g, 0.100 mole) in dry tetrahydrofuran (50 mL) was added over 25 minutes, and stirring was continued for 40 minutes. Water (4.0 mL) was then added, followed by 3.0M aqueous sodium hydroxide (34 mL), followed by 30% aqueous hydrogen peroxide (34 mL). After the mixture was warmed to room temperature, it was extracted with ether. The residue was chromatographed with 1:1 ether/hexane and recrystallized (cyclohexane) to provide the title compound (16.10 g, 55%) as a white solid, mp 80°-81°.

Workup

  1. stirringstirring
  2. waitwas continued for 40 minutes
  3. extractionit was extracted with ether
  4. customThe residue was chromatographed with 1:1 ether/hexane
  5. customrecrystallized (cyclohexane)

Sources & evidence

ORD record
ord-25fd08ce5e634355936808545e0f12c2
Source dataset
uspto-grants-1989_05
Patent number
US04833164

Reaction notes

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