1,5-Dimethylbicyclo[3.2.1]octan-8-one → 1,5-Dimethylbicyclo[3.2.1]octan-8-one oxime

HRID 2164212Notes

Reaction equation

HRID 2164212 reaction equation
[CH3:1][C:2]12[C:9](=O)[C:6]([CH3:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.S(O)(O)(=O)=O.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>O>[CH3:1][C:2]12[C:9](=[N:17][OH:18])[C:6]([CH3:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 895551,5-Dimethylbicyclo[3.2.1]octan-8-oneHCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium Acetate

Product 1

HCID 1664501,5-Dimethylbicyclo[3.2.1]octan-8-one oximeYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

At 60° C., 91.2 g (0.6 mole) of 1.5-dimethyl-bicyclo[3.2.1]octane-8-one (1) was dripped into a solution of 78.7 g (0.6 mole) hydroxylamin hydrogensulfate and 54.2 g (0.66 mole) sodium acetate in 135 g water. This was stirred for 1 h at 60° C. and then allowed to cool to room temperature and sodium extracted with ether. The combined organic phases were neutralized by washing with a saturated solution of chloride, dried and concentrated by evaporation. 95 g (95%) 2 crystalline solid is obtained. By crystallising 9 g of the raw product from 15 ml ethanol, 8 g 2 are obtained having a m.p. of 129°-130° C. IR: 3400, 3250, 1685, 930 cm-1 (oxim). NMR (CCl4): δ=1.05, s (--CH3, transoid to --C=N--OH), 1.43, s (--CH3, cisoid to -- C=N--OH), 9.03 ppm (--C=N--OH). MS: m/z (%)=167 (M+, 2%), 150(85), 133(15), 123(17), 108(23), 93(100). C10H17ON (M: 167.24)

Workup

  1. customAt 60° C.
  2. temperatureto cool to room temperature
  3. extractionsodium extracted with ether
  4. washby washing with a saturated solution of chloride
  5. customdried
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2a1323c5e47d4ab384d2bd5ef08524d1
Source dataset
uspto-grants-1985_03
Patent number
US04502985

Reaction notes

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