Hydrogen Peroxide → HCID 13187533, compound

HRID 1021199Notes

Reaction equation

HRID 1021199 reaction equation
[CH2:1]([C:5]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[C:8]([CH3:14])=[C:7]([CH3:15])[C:6]=1[O:16][CH3:17])[CH2:2][CH:3]=[CH2:4].C12BC(CCC1)CCC2.[OH-].[Na+].OO.B.C([O-])([O-])=[O:33].[K+].[K+].C(OC(C)C)(=O)C>C1COCC1>[CH3:17][O:16][C:6]1[C:7]([CH3:15])=[C:8]([CH3:14])[C:9]([O:12][CH3:13])=[C:10]([CH3:11])[C:5]=1[CH2:1][CH2:2][CH2:3][CH2:4][OH:33]

Participants

9

Reactant 7

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 7915Isopropyl AcetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 86653772HCID 86653772, compound

Product 1

HCID 13187533HCID 13187533, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(But-3-enyl)-2,5-dimethoxy-3,4,6-trimethylbenzene (5.08 g) in 50 mL THF was treated with 9-borabicyclo[3.3.1]nonane (9-BBN) (2.96 g) and stirred overnight at room temperature. A chilled solution of 10 M NaOH (10 mL) and 35% w/w H2O2 (10 mL) was added to cold borane (0° C.) such that the internal temperature never exceeded 36° C. The cloudy solution was stirred vigorously and treated with 2 g K2CO3 until the layers clarified. Isopropyl acetate (100 mL) was added followed by separation and extraction of the aqueous phase 3×60 mL isopropyl acetate. The combined organics were washed with 50 mL saturated NaCl, dried over Na2SO4 and concentrated to a pale yellow oil. Flash chromatography yielded 3.3 g of 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)butan-1-ol as a white powder (60.3%). Mp 85.1-87.1° C.; 1H NMR (400 MHz, CDCl3) δ=3.67 (m, 5H), 3.64 (s, 3 H), 2.63 (q, 2 H), 2.22 (s, 3 H), 2.17 (s, 6 H), 1.68 (m, 2 H), 1.55 (m, 2 H) ppm.

Workup

  1. stirringThe cloudy solution was stirred vigorously
  2. customfollowed by separation and extraction of the aqueous phase 3×60 mL isopropyl acetate
  3. washThe combined organics were washed with 50 mL saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a pale yellow oil

Sources & evidence

ORD record
ord-fbec3f4a349246629552b330610d3707
Source dataset
uspto-grants-2014_05
Patent number
US08716527B2

Reaction notes

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