Hydrogen Peroxide → HCID 11357716, compound

HRID 2101238Notes

Reaction equation

HRID 2101238 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][C:4]([C:7](=[O:13])[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:3][CH:2]=1.B(F)(F)F.CC[O:26]CC.[OH-].[Na+].OO.C([O-])([O-])=O.[K+].[K+]>[BH4-].[Na+].COCCOCCOC.O>[C:1]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:2]=[CH:3][C:4]([CH:7]([OH:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:26])=[CH:5][CH:6]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57801035HCID 57801035, compound

Product 1

HCID 11357716HCID 11357716, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8150DiglymeSolvent2×HCID 4311764Sodium borohydrideSolvent

Procedure

1-Biphenyl-4-yl-hex-5-en-1-one (1 g) was dissolved in 0.5 M NaBH4 in diglyme (9 ml) and chilled in an ice bath. BF3.OEt2 (1 ml) in diglyme (4 ml) was added with vigorous stirring. Stirring was continued for 1 hour and water (1 ml) was added. 3M NaOH (2 ml) was added followed by 30% H2O2 (3 ml). Anhydrous K2CO3 (5 g) was added and the solvent decanted. The K2CO3 was washed with ethyl acetate and the combined organics dried (Na2SO4) and evaporated. Distillation under vacuum (oil bath temperature 175° C.) removed most of the remaining diglyme. The residue was purified by column chromatography (light petroleum:diethyl ether 2:1) to give a clear oil which solidified to give the title compound as a white powder (65%). δC (CDCl3, 62.9 MHz): 25.6, 25.7, 32.6, 39.0, 62.8, 74.2, 126.4, 127.1, 127.2, 127.3, 128.8, 140.4, 140.8 and 143.9. δH (CDCl3, 250 MHz): 1.39 (4H, m), 1.54 (2H, m), 1.81 (2H, m), 2.11 (1 or 2H, s), 3.37 (0 or 1H, s), 3.60 (2H, m), 4.69 (1H, t, J 6.4), 7.40 (5H, m) and 7.56 (4H, m). GCMS (EI+) (Found M, 270. C18H22O2 requires 270).

Workup

  1. temperaturechilled in an ice bath
  2. customthe solvent decanted
  3. washThe K2CO3 was washed with ethyl acetate
  4. dry with materialthe combined organics dried (Na2SO4)
  5. customevaporated
  6. distillationDistillation under vacuum (oil bath temperature 175° C.)
  7. customremoved most of the remaining diglyme
  8. customThe residue was purified by column chromatography (light petroleum:diethyl ether 2:1)
  9. customto give a clear oil which

Sources & evidence

ORD record
ord-87a37bfafa5a4e7aa0ef7032630709fa
Source dataset
uspto-grants-2009_08
Patent number
US07572825B2

Reaction notes

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