Reaction #742284

Reaction equation

2,5-Dimethyl-bicyclo[3.2.1]oct-2-ene

peracetic acid

sodium acetate

→

2,6-dimethyl-3-oxa-tricyclo[4.2.1.0*2,4*]nonane

Yield 82.0%

Conditions

Workup

1. 1
   Othersubsequently quenched with water and toluene
2. 2
   Othersplit
3. 3
   WashThe organic layer was first washed with a solution of sodium carbonate (Na2CO3)
4. 4
   workup.DISTILLATIONFractional distillation of the organic layer

Procedure

2,5-Dimethyl-bicyclo[3.2.1]oct-2-ene (800 g, 5.88 mol, obtained as above in EXAMPLE I) was fed into a solution of peracetic acid (CH3CO3H, 32%, 1.466 Kg, 6.18 mol) and sodium acetate (CH3CO2Na, 72 g, 0.882 mol), and cooled to 0° C. The reaction mixture was aged for 6 hours, and subsequently quenched with water and toluene. The reaction mixture was shaken and split. The organic layer was first washed with a solution of sodium carbonate (Na2CO3), and then with a solution of sodium sulfite (Na2SO3). Fractional distillation of the organic layer provided 2,6-dimethyl-3-oxa-tricyclo[4.2.1.0*2,4*]nonane (734 g) having a boiling point of 31° C. at a pressure of 18 mmHg

Source