Diethyl Ether → HCID 66974043, compound

HRID 1948751Notes

Reaction equation

HRID 1948751 reaction equation
[CH3:1][C:2]12[O:9][CH:8]1[CH2:7][C:6]1([CH3:11])[CH2:10][CH:3]2[CH2:4][CH2:5]1.B(F)(F)F.O(CC)CC>C1(C)C=CC=CC=1>[CH3:11][C:6]12[CH2:10][CH:3]([CH2:4][CH2:5]1)[CH:2]([CH3:1])[C:8](=[O:9])[CH2:7]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6356Boron trifluoride3×HCID 87222066HCID 87222066, compound

Product 1

HCID 66974043HCID 66974043, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

2,6-Dimethyl-3-oxa-tricyclo[4.2.1.0*2,4*]nonane (381 g, 2.51 mol, obtained as above in EXAMPLE II) was fed into a solution of boron trifluoride diethyletherate (BF3.O(C2H5)2, BF3, 35 g, 0.251 mol) in toluene (500 mL) while the pot temperature was maintained at about 30° C. and the aging process continued for 6 hours. The reaction mixture was subsequently quenched with water and washed with a Na2CO3 solution. Fractional distillation of the organic layer provided 1,4-dimethyl-bicyclo[3.2.1]octan-3-one (337 g) having a boiling point of 43° C. at a pressure of 1 mmHg.

Workup

  1. customThe reaction mixture was subsequently quenched with water
  2. washwashed with a Na2CO3 solution
  3. distillationFractional distillation of the organic layer

Sources & evidence

ORD record
ord-c62c53f4c2e3475f867f0ff342de7eb4
Source dataset
uspto-grants-2013_03
Patent number
US08399522B2

Reaction notes

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