Hydrogen Peroxide → HCID 178448129, compound

HRID 1419804Notes

Reaction equation

HRID 1419804 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)([CH3:3])=[CH2:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[OH-].[Na+].OO>C1COCC1.C(Cl)Cl.O.C(O)C>[C:1]([C@@H:4]1[CH2:9][CH2:8][C@H:7]([OH:10])[CH2:6][CH2:5]1)([CH3:3])=[CH2:2]

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 5492914-(1-Methylethenyl)cyclohexanoneHCID 3611392Lithium tri-s-butylborohydride

Product 1

HCID 178448129HCID 178448129, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4.7 g (0.034 mol) of 4-isopropenylcyclohexanone dissolved in 35 ml of THF were added dropwise to 39 ml of a 1 molar solution at -78° C. of L-Selectride in THF. The mixture was subsequently stirred at -78° for 3 hours and then heated to room temperature, and 5 ml of H2O, 20 ml of ethanol, 15 ml of 6N NaOH and 17 ml of 35% strength H2O2 solution were added in succession. Water was added to the reaction solution, and extraction was carried out with methylene chloride. The combined methylene chloride phases are dried and concentrated. 37 g (78% of theory) of product remained as a colorless oil. The cis/trans mixture produced (>90% cis) was reacted further without additional purification.

Workup

  1. dry with materialThe combined methylene chloride phases are dried
  2. concentrationconcentrated
  3. customThe cis/trans mixture produced (>90% cis)
  4. customwas reacted further without additional purification

Sources & evidence

ORD record
ord-348d230a333249368bd280ef1e33afb5
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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