Water → HCID 12767935, compound

HRID 895000Notes

Reaction equation

HRID 895000 reaction equation
[CH3:1][C:2]12[CH2:11][CH2:10][CH:5]([CH2:6][C:7]1=NO)[CH:4]([CH3:12])[O:3]2.N([O-])=[O:14].[Na+].O.S(=O)(=O)(O)O>C(OCC)C>[CH3:1][C:2]12[CH2:11][CH2:10][CH:5]([CH2:6][C:7]1=[O:14])[CH:4]([CH3:12])[O:3]2

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 86737964HCID 86737964, compound

Product 1

HCID 12767935HCID 12767935, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 20.5 g. 1,3-dimethyl-2-oxabicyclo[2,2,2]octan-6-one-oxime, 16 g. sodium nitrite, 350 ml. water and 100 ml. diethylether at 25° C. there is added dropwise 100 ml. of 2 N sulfuric acid and the mixture is allowed to stand with occasional stirring for 3 hours. The organic layer is washed with 10% aqueous sodium bicarbonate and evaporated. To the resulting residue at 0° C. there is added 70 ml. concentrated ammonium hydroxide. This mixture is then extracted several times with diethyl ether and the combined ether extracts are dried over magnesium sulfate and evaporated to give 1,3-dimethyl-2-oxabicyclo[2,2,2]octan-6-one.

Workup

  1. additionTo a mixture of 20.5 g
  2. washThe organic layer is washed with 10% aqueous sodium bicarbonate
  3. customevaporated
  4. additionTo the resulting residue at 0° C. there is added 70 ml
  5. extractionThis mixture is then extracted several times with diethyl ether
  6. dry with materialthe combined ether extracts are dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-653ab34bf61948e09ee7ccbf55ad019c
Source dataset
uspto-grants-1981_08
Patent number
US04285944

Reaction notes

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