Allyl bromide → HCID 23117514, compound

HRID 1163476Notes

Reaction equation

HRID 1163476 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH3:9])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:26](Br)[CH:27]=[CH2:28]>C(Cl)Cl.O1CCCC1.O.[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:26]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:6][CH:5]=[CH2:4])=[CH:12][CH:11]=2)([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:7][CH:2]=[CH2:3])=[CH:21][CH:22]=2)[CH3:9])=[CH:4][CH:3]=1)[CH:27]=[CH2:28]

Participants

8

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 931181,1,1-Tris(4-hydroxyphenyl)ethane

Product 1

HCID 23117514HCID 23117514, compound

Reagents, catalysts & solvents 4

HCID 2724163Tetraphenylphosphonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 500 mL three neck-round bottom flask equipped with condenser, magnetic stirring bar, dropping funnel, and Argon inlet, 15.00 g (49 mmol) of 1,1,1tris(4-hydroxy-phenyl)ethane was dissolved in a 1:1 mixture of methylene chloride and tetrahydrofuran. To this mixture, a solution of sodium hydroxide 10.70 g (267 mmol) dissolved in 60 mL of distilled water was added while vigorously stirring. Allyl bromide, 33.36 g (276 mmol) was added followed by 2.5 g (5.96 mmol) tetraphenylphosphoniumbromide catalyst. The reaction mixture was left under positive pressure of Argon while stirring at room temperature. The reaction was monitored by TLC and stopped after 36 hours. The reaction mixture was transferred into separatory funnel and the product was extracted twice with 200 mL of methylene chloride. The organic layers were combined and extensively washed several times with distilled water. The organic extract was dried over anhydrous magnesium sulfate and filtered using Whatman filter paper. To this filtrate, activated charcoal was added and the mixture was stirred for 12 h. The charcoal was filtered and the solvent was evaporated using rotary evaporator. The resulting viscous compound was purified through column chromatography using silica as stationary phase and methylene chloride as an eluent. The solvent was removed using rotary evaporator to yield 14.50 g (70%) of clear, colorless, viscous liquid of 1,1,1tris(4-allyloxy-phenyl)ethane. 1H NMR and IR spectra were consistent with 1,1,1tris(4-allyloxy-phenyl)ethane. 1H NMR (CDCl3): 4.58 (m, CH2O, 6 H), 2.17 (s, —CH3), 5.2 (m, ═CH2, 6 H), 6.1 (m, ═CH, 3 H), 6.81 (dd, 6 aromatic H ortho to OR, 7.03 (dd, 6 aromatic H meta to OR). IR (NaCl): Major bands at 1293 cm−1 (aromatic ether), 2912 cm−1 (aliphatic hydrocarbon), and 1648 cm−1 (unsaturated hydrocarbon).

Workup

  1. additionwas added
  2. waitThe reaction mixture was left under positive pressure of Argon
  3. stirringwhile stirring at room temperature
  4. customThe reaction mixture was transferred into separatory funnel
  5. extractionthe product was extracted twice with 200 mL of methylene chloride
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. filtrationfilter paper
  10. additionTo this filtrate, activated charcoal was added
  11. stirringthe mixture was stirred for 12 h
  12. filtrationThe charcoal was filtered
  13. customthe solvent was evaporated
  14. customevaporator
  15. customThe resulting viscous compound was purified through column chromatography
  16. customThe solvent was removed
  17. customevaporator

Sources & evidence

ORD record
ord-caa1482647094c5593535bd72abc899b
Source dataset
uspto-grants-2010_10
Patent number
US07821719B2

Reaction notes

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