Trimethylamine oxide dihydrate → HCID 20230968, compound

HRID 2290497Notes

Reaction equation

HRID 2290497 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH2:7][C:6]([CH3:14])=[CH:5][CH2:4][C:3]1=2.[OH2:16].[OH2:17].C[N+]([O-])(C)C>C(O)(C)(C)C.O.[Os](=O)(=O)(=O)=O>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH2:7][C:6]([CH3:14])([OH:16])[CH:5]([OH:17])[CH2:4][C:3]1=2

Participants

6

Reactant 2

HCID 198430Trimethylamine oxide dihydrateHCID 20222588HCID 20222588, compound

Product 1

HCID 20230968HCID 20230968, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

253.3 g of hydrocarbon mixture containing about 60% of 2,2,5,5,8-pentamethyl-bicyclo[4.4.0]deca-1(6),8-diene are dissolved in 1050 ml of tert.butanol and treated with a solution of 91.65 g of trimethylamine N-oxide dihydrate in 375 ml of water. Thereto there is added a solution of 40 mg of osmium tetroxide in 75 ml of tert.butanol and the mixture is held for 48 hours at 95° C. with good stirring at reflux temperature. The solution is extracted with 2 l of dichloromethane, 1 l of water and 412.5 ml of 2N hydrochloric acid and ice. The organic phase is washed neutral twice with 1 l of water each time and the aqueous phases are extracted with dichloromethane. After drying over magnesium sulphate and concentration on a rotary evaporator, there are obtained 269 g of crude crystals. These are recrystallized from 150 ml of hexane and 80 ml of dichloromethane. There are obtained 167.0 g of crystalline 2,2,5,5,8-pentamethyl-bicyclo[4.4.0]dec-1(6)-ene-8,9-diol of melting point 98°-99.5° C.

Workup

  1. temperatureat reflux temperature
  2. extractionThe solution is extracted with 2 l of dichloromethane, 1 l of water and 412.5 ml of 2N hydrochloric acid and ice
  3. washThe organic phase is washed neutral twice with 1 l of water each time
  4. extractionthe aqueous phases are extracted with dichloromethane
  5. dry with materialAfter drying over magnesium sulphate and concentration on a rotary evaporator, there
  6. customare obtained 269 g of crude crystals
  7. customThese are recrystallized from 150 ml of hexane and 80 ml of dichloromethane

Sources & evidence

ORD record
ord-126bb8f31ed54f9fbea6095e22ea06a8
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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