Allyl bromide → HCID 19027295, compound

HRID 2256775Notes

Reaction equation

HRID 2256775 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH:2]=C.OCCOCC[O:27][C:28]1C=CC(C([O-])=O)=[CH:30][CH:29]=1.[H-].[Na+].[H][H].C(Br)C=C>O1CCCC1.O>[CH2:28]([O:27][CH2:2][CH2:1][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH:29]=[CH2:30]

Participants

8

Reactant 5

HCID 7841Allyl bromideHCID 24758Sodium hydride2×HCID 19027301Methyl 4-(2-{2-[(prop-2-en-1-yl)oxy]ethoxy}ethoxy)benzoateHCID 19027304HCID 19027304, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19027295HCID 19027295, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

These compounds were synthesized by similar methods. The representative synthesis of methyl 4-(2-(2-allyloxy-ethoxy)ethoxy)benzoate (7) is presented. The obtained methyl 4-(2-(2-hydroxyethoxy) ethoxy) benzoate (3) 8.4 grams (0.035 mole) was added to a suspension of 3.15 grams (0.105 mole) sodium hydride in 100 ml dried tetrahydrofuran at 4° C. After the hydrogen was completely released, allyl bromide 3.94 ml (0.0456 mole) was added dropwise to the reaction mixture and then stirred at room temperature overnight. The excess sodium hydride was treated with distilled water and extracted with ethyl acetate. The organic phase was washed with 10% aqueous hydrochloric acid solution, dried over anhydrous MgSO4, and the solvent evaporated on a rotary evaporator. The yellow oil product was purified by flash chromatography on silica gel with 4% diethyl ether in dischloromethane. Yield 8.39 grams (86%). 1H-NMR (CDCl3, TMS): d=3.81-4.25 (m, 10H, --CH2 --(OCH2CH2)2 --), 3.85 (s, 3H, --COOCH3), 5.23 and 5.9 (m, 3H, CH=CH--), 6.95 and 8.05 (2d, 4 aromatic protons).

Workup

  1. customThese compounds were synthesized by similar methods
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with 10% aqueous hydrochloric acid solution
  4. dry with materialdried over anhydrous MgSO4
  5. customthe solvent evaporated on a rotary evaporator
  6. customThe yellow oil product was purified by flash chromatography on silica gel with 4% diethyl ether in dischloromethane

Sources & evidence

ORD record
ord-729aa6f2ceaa4ed9a9d903397d05d89b
Source dataset
uspto-grants-1997_08
Patent number
US05656197

Reaction notes

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