Hydrochloric Acid → HCID 54447559, compound

HRID 975256Notes

Reaction equation

HRID 975256 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6]/[C:7](/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[N:8]/[OH:9].[Br:16][CH2:17][CH2:18]Br.[OH-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[Br:16][CH2:17][CH2:18][O:9][N:8]=[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 19971654HCID 19971654, compound

Product 1

HCID 54447559HCID 54447559, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of the above oxime (6.5 g, 31 mmol), 1,2-dibromoethane (27 ml, 31 mmol), N,N,N,N-tetrabutylammonium bromide (0.96 g, 3 mmol) and 12N sodium hydroxide (30 ml) was cooled on an icebath with vigorous stirring until the initial exotherm had subsided. The mixture was then stirred at ambient temperature for 16 h. Water (50 ml), 4 N hydrochloric acid (50 ml) and dichloromethane (100 ml) were added and the phases were separated. To the organic phase was added water (50 ml) and pH in the aqueous phase adjusted to 5 with 10% aqueous citric acid. The organic phase was washed with water (50 ml), brine (25 ml) and dried (Na2SO4). The solvent was evaporated in vacuo to give 9.1 g of 5-methoxy-1-phenyl-1-pentanone O-(2-bromoethyl)oxime.

Workup

  1. temperaturewas cooled on an icebath
  2. stirringThe mixture was then stirred at ambient temperature for 16 h
  3. customthe phases were separated
  4. additionTo the organic phase was added water (50 ml)
  5. washThe organic phase was washed with water (50 ml), brine (25 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3066d992e0304c888db3e40a576c7fa9
Source dataset
uspto-grants-1997_03
Patent number
US05608069

Reaction notes

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