Benzyl Bromide → HCID 53941180, compound

HRID 1729763Notes

Reaction equation

HRID 1729763 reaction equation
[CH2:1]([O:4][NH:5][C:6](=[C:9]1[C:14](=[O:15])[CH2:13][C:12]([CH3:17])([CH3:16])[CH2:11][C:10]1=[O:18])[CH2:7][CH3:8])[CH:2]=[CH2:3].[OH-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CC(C)=O.O>[CH2:1]([O:4][N:5]=[C:6]([C:9]1[C:10](=[O:18])[CH2:11][C:12]([CH3:17])([CH3:16])[CH2:13][C:14]=1[O:15][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:7][CH3:8])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 178460138HCID 178460138, compound

Product 1

HCID 53941180HCID 53941180, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(1-allyloxyaminopropylidene)-5,5-dimethylcyclohexane-1,3-dione (2.5 g) in acetone (30 ml), sodium hydroxide (0.4 g) in water (2 ml) was added at room temperature and then benzyl bromide (2.0 g) was added. After stirring for 10 hours at 60° C the reaction mixture was poured into ice-water and extracted with chloroform. The extract was washed with one normal sodium hydroxide and dried over magnesium sulfate. The solvent was removed in vacuo and an oily substance which solidified on standing at 0° C was obtained. Recrystallization from the mixture of methanol and water gave the desired product as crystal.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with one normal sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customon standing at 0° C
  6. customwas obtained
  7. customRecrystallization
  8. additionfrom the mixture of methanol and water

Sources & evidence

ORD record
ord-1c3cfa3ef17344c18b1f5d1a45478ddf
Source dataset
uspto-grants-1976_11
Patent number
US03989737

Reaction notes

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