Water → HCID 522153, compound

HRID 1265981Notes

Reaction equation

HRID 1265981 reaction equation
Br[CH:2]1[CH2:4][C:3]1([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CC(C)([O-])C.[K+].C(OCC)C.O>CS(C)=O>[CH3:11][C:3]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:4]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 582928HCID 582928, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 522153HCID 522153, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
72 °C

Procedure

To a solution of 1.56 g (0.00739 mol) of 2-bromo-1-methyl-1-phenylcyclopropane in 5 ml of dimethylsulfoxide was added 1.429 g (0.0127 mol) of potassium tert-butoxide. After the reaction was heated to 72° C. for 4 hours, diethyl ether and water were added. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 0.88 g of 70% pure 3-methyl-3-phenylcyclopropene as an oil. The major byproduct (roughly 20%) was 1-methyl-1-phenylcyclopropane.

Workup

  1. customThe resulting mixture was transferred to a separatory funnel
  2. customthe phases were separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-ed83dd0b5e504b129a749cd1d1a2b49a
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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