Allyl bromide → HCID 22394942, compound

HRID 1071779Notes

Reaction equation

HRID 1071779 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CC(C)=O>[CH2:23]([O:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:7])=[CH:4][CH:3]=1)[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetate

Product 1

HCID 22394942HCID 22394942, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

1.62 g (8.39 mmol) ethyl 4-hydroxybenzoylformate and 5.79 g (42 mmol) K2CO3 are dissolved in 70 ml acetone. 1.22 g (10.1 mmol) allyl bromide is added dropwise at room temperature. The mixture is heated at 40° C. for 3.25 hours under nitrogen atmosphere. The mixture is then filtered and evaporated. The phases are separated and water is extracted with toluene. The organic phases are dried over magnesium sulfate. Evaporation of the solvent and chromatography (eluent: hexane ethyl acetate 3:1) give 1.39 g (71 wt %) of a yellow oil.

Workup

  1. filtrationThe mixture is then filtered
  2. customevaporated
  3. customThe phases are separated
  4. extractionwater is extracted with toluene
  5. dry with materialThe organic phases are dried over magnesium sulfate
  6. customEvaporation of the solvent and chromatography (eluent: hexane ethyl acetate 3:1)
  7. customgive 1.39 g (71 wt %) of a yellow oil

Sources & evidence

ORD record
ord-3750e931baf3485fb68b82c8416d899d
Source dataset
uspto-grants-2005_06
Patent number
US06906113B2

Reaction notes

Loading…