Chloride → HCID 131711430, compound

HRID 1390860Notes

Reaction equation

HRID 1390860 reaction equation
[Cl-].[CH3:2][O:3][C:4]1([O:14][CH3:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[N:12][OH:13].Cl.[Br:17]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[Br:17][CH:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5](=[N:12][OH:13])[C:4]1([O:3][CH3:2])[O:14][CH3:15]

Participants

7

Reactant 5

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24408BromineHCID 71371084N-(2,2-Dimethoxycyclooctylidene)hydroxylamine

Product 1

HCID 131711430HCID 131711430, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Following the general procedure of Example 1, but using diethyl ether as a solvent in place of methylane chloride, to a solution of 5.025 parts of 2,2-dimethoxycyclooctanone oxime in 28 parts of diethyl ether was added 1.7 parts anhydrous hydrogen chloride at about 32° C. The mixture was stirred and to this was added about 4 parts bromine dissolved in 7 parts diethyl ether over a 5 minute period. After the addition the mixture was allowed to stir for about 0.5 hour. The mixture was then treated with aqueous sodium carbonate to remove dissolved acids in the ether layer and then worked with water. The ether phase was then dried and then distilled under vacuum to yield 50 percent of theory of 3-bromo-2,2-dimethoxycyclooctanone oxime as determined by nuclear magnetic resonance spectroscopy.

Workup

  1. additionAfter the addition the mixture
  2. stirringto stir for about 0.5 hour
  3. customto remove
  4. dissolutiondissolved acids in the ether layer
  5. dry with materialThe ether phase was then dried
  6. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-a019ebec1afc484b9496841ebc834744
Source dataset
uspto-grants-1979_02
Patent number
US04140717

Reaction notes

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