Hydrogen Peroxide → HCID 11484593, compound

HRID 1817679Notes

Reaction equation

HRID 1817679 reaction equation
[CH2:1]([O:6][CH:7]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[CH2:2][CH2:3][CH2:4][CH3:5].B(F)(F)F.CC[O:31]CC.[OH-].[Na+].OO.C([O-])([O-])=O.[K+].[K+]>[BH4-].[Na+].COCCOCCOC.O>[C:16]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:18][C:13]([CH:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:31])=[CH:14][CH:15]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 57801040HCID 57801040, compound

Product 1

HCID 11484593HCID 11484593, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8150DiglymeSolvent2×HCID 4311764Sodium borohydrideSolvent

Procedure

4-(1-pentyloxyhex-5-enyl)-biphenyl (1 g) was dissolved in 0.5 M NaBH4 in diglyme (8 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 removes most of the remaining diglyme. The residue was purified by column chromatography (ethyl acetate/petrol) to give an oil. δC (CDCl3, 62.9 MHz): 14.1, 22.6, 25.7, 25.8, 28.4, 29.7, 32.7, 34.4, 63.0, 69.0, 82.0, 126.9, 127.1, 127.2, 128.8, 140.2, 141.0 and 142.4. δH (CDCl3, 250 MHz): 0.88 (3H, m), 1.16-1.55 (14H, m), 3.30 (2H, m), 3.62 (2H, t, J 6.1), 4.21 (1H, t, J 6.1), 7.34 (3H, d, J 7.6), 7.43 (2H, t, J 7.3) and 7.58 (4H, t, J 7.3).

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
  7. customremoves most of the remaining diglyme
  8. customThe residue was purified by column chromatography (ethyl acetate/petrol)
  9. customto give an oil

Sources & evidence

ORD record
ord-6471a3ec7b334709a6c7a5e6ad7d6304
Source dataset
uspto-grants-2009_10
Patent number
US07598289B2

Reaction notes

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