Allyl bromide → HCID 131724626, compound

HRID 393493Notes

Reaction equation

HRID 393493 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([C:11]([OH:13])=[O:12])=[C:4]([CH3:14])[C:3]=1[OH:15].Br[CH2:17][CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([C:11]([OH:13])=[O:12])=[C:4]([CH3:14])[C:3]=1[O:15][CH2:19][CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 129858547HCID 129858547, compound

Product 1

HCID 131724626HCID 131724626, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.400 g (11.42 mmol) of dimethyl 5-hydroxyisophthalic acid, 1.4 g (11.6 mmol) of 3-bromopropene and 1.6 g (11.6 mmol) of potassium carbonate were dispersed in 40 ml of acetone and stirred for 15 hours at reflux temperature. The mixture was cooled to room temperature and filtered off insoluble salts after the addition of 150 ml of diethylether. The filtrate was concentrated and purified through the silicagelcolumn chromatography (developing solvent: diethylether/hexane=½), 2.612 g of dimethyl 5-allyloxyisophthalic acid in water-white solid powder was obtained (yield: 94.1%).

Workup

  1. temperatureat reflux temperature
  2. filtrationfiltered off insoluble salts
  3. additionafter the addition of 150 ml of diethylether
  4. concentrationThe filtrate was concentrated
  5. custompurified through the silicagelcolumn chromatography (developing solvent: diethylether/hexane=½)

Sources & evidence

ORD record
ord-3f89363c6a0b4a7fa7a3aa60be53f373
Source dataset
uspto-grants-2004_10
Patent number
US06808766B1

Reaction notes

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