1,2-Dichloroethane → 2-Oxabicyclo[2.2.2]octan-6-one, 1,3,3-trimethyl-

HRID 426576Notes

Reaction equation

HRID 426576 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:11])([CH3:10])[CH3:9])[CH2:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:20])C=1.C(Cl)CCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]12[CH2:7][CH2:6][CH:5]([CH2:4][C:3]1=[O:20])[C:8]([CH3:10])([CH3:9])[O:11]2

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 70297m-Chloroperbenzoic acidHCID 443162(L)-alpha-TerpineolHCID 178418287HCID 178418287, compound

Product 1

HCID 1122032-Oxabicyclo[2.2.2]octan-6-one, 1,3,3-trimethyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.08 g. (0.02 mole) α-terpineol and 4.45 g. (0.022 mole) of 85 percent m-chloroperbenzoic acid in 70 ml. of ethylene dichloride is refluxed under nitrogen for 20 hours, then cooled to room temperature and washed with aqueous sodium bisulfite and sodium bicarbonate solutions. The solvent is removed in vacuo and the resulting oil is treated in situ with 2.94 g. (0.0136 mole) pyridinium chlorochromate. The resulting mixture is stirred under nitrogen in 35 ml. of methylene chloride at ambient temperatures for 2.5 hours. After addition of 200 ml. diethyl ether, the mixture is filtered through celite and the solvent evaporated to give, on steam distillation, 1,3,3-trimethyl-2-oxabicyclo [2,2,2]octan-6-one; m.p. 50° to 52° C.

Workup

  1. additionA mixture of 3.08 g
  2. washwashed with aqueous sodium bisulfite and sodium bicarbonate solutions
  3. customThe solvent is removed in vacuo
  4. additionthe resulting oil is treated in situ with 2.94 g
  5. additionAfter addition of 200 ml
  6. filtrationdiethyl ether, the mixture is filtered through celite
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-f5359b997e454ac181e33e29059008cf
Source dataset
uspto-grants-1979_10
Patent number
US04170599

Reaction notes

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