Sodium Carbonate → 4,7,7-Trimethylbicyclo[4.1.0]hept-4-en-3-one

HRID 848430Notes

Reaction equation

HRID 848430 reaction equation
[CH:1]12[C:7]([CH3:9])([CH3:8])[CH:6]1[CH2:5][CH:4]=[C:3]([CH3:10])[CH2:2]2.N(Cl)=[O:12].C(=O)([O-])[O-].[Na+].[Na+].C12C(C)(C)C1CC(=NO)C(C)=C2.S(=O)(O)[O-].[Na+]>C(O)C>[CH:1]12[C:7]([CH3:9])([CH3:8])[CH:6]1[CH2:5][C:4](=[O:12])[C:3]([CH3:10])=[CH:2]2

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 17601Nitrosyl chlorideHCID 260493-CareneHCID 571772HCID 571772, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 126529134,7,7-Trimethylbicyclo[4.1.0]hept-4-en-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material 2-caren-4-one can be produced from commercially available, optically pure (+)-3-carene. The (+)-3-carene is treated with nitrosyl chloride followed by the addition of powdered sodium carbonate. The resulting 2-caren-4-one oxime is then treated with sodium bisulfite in aqueous ethanol to yield 2-caren-4-one, the desired starting product for the inventive process.

Sources & evidence

ORD record
ord-31bd34f315bc43ddb229dd3ac6dd9fc2
Source dataset
uspto-grants-1981_10
Patent number
US04296038

Reaction notes

Loading…