Sodium Iodide → Ethyl 3-{4-[(prop-2-en-1-yl)oxy]phenyl}propanoate

HRID 1637302Notes

Reaction equation

HRID 1637302 reaction equation
[C:1]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:2][CH2:3][C:4]1[CH:10]=[CH:9][C:7]([OH:8])=[CH:6][CH:5]=1.[CH2:15](Br)[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH2:17]([O:8][C:7]1[CH:9]=[CH:10][C:4]([CH2:3][CH2:2][C:1]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:6]=1)[CH:16]=[CH2:15]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 2736435Ethyl 4-hydroxyhydrocinnamate

Product 1

HCID 19348971Ethyl 3-{4-[(prop-2-en-1-yl)oxy]phenyl}propanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

38.8 g (0.2 mol) of ethyl phloretate (prepared from commercial phloretic acid (e.g. Merck, D-64271 Darmstadt, DE) by esterification with ethanol) were dissolved in 20 ml of acetone, and 36.3 g (0.3 mol) of allyl bromide, 48.3 g (0.35 mol) of potassium carbonate and 0.05 g of sodium iodide were added. The mixture was heated at reflux for 7 h and cooled, and the excess of carbonate was filtered off. Concentration of the filtrate gave ethyl 3-(4-allyloxyphenyl)propionate, which was hydrolyzed in customary manner with methanolic potassium hydroxide to give the free acid. Customary reaction of the acid with thionyl chloride in toluene at 80° C. gave the 3-(4-allyloxyphenyl)propionyl chloride (b.p. 0.01 hPa: 106-108° C.) in 93% yield. 51.2 g (0.22 mol) of this acid chloride and 39.2 g (0.22 mol) of hydroquinone monomethacrylate were dissolved in 300 ml of toluene at 65° C. 24.0 g (0.24 mol) of triethylamine were added dropwise with stirring, and the mixture was subsequently stirred for 3 h. After cooling, the amine hydrochloride was filtered off and the filtrate was worked up in a customary manner. Concentration of the organic residue and recrystallization of the solid residue from toluene/benzine (b.p. 100-140) gave 4-methacryloyloxyphenyl) 3-(4-allyloxyphenyl)propionate in 80% yield. The ester melts at 67° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 h
  3. temperaturecooled
  4. filtrationthe excess of carbonate was filtered off

Sources & evidence

ORD record
ord-5a69bd452e2a49fc80cee1d1d38c09ce
Source dataset
uspto-grants-2000_03
Patent number
US06040411

Reaction notes

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