Hydrochloric Acid → Benzylvinylether

HRID 2108324Notes

Reaction equation

HRID 2108324 reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2C=C1)C3.C(C(Cl)C1C=CC=CC=1)=C.[N+]([C:24]1C=C([N+]([O-])=O)C=C[C:25]=1[OH:33])([O-])=O.[OH-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(C(C)=O)C>[CH:25]([O:33][CH2:1][C:5]1[CH:4]=[CH:8][CH:9]=[CH:10][CH:6]=1)=[CH2:24]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14932,4-DinitrophenolHCID 6492DicyclopentadieneHCID 14798Sodium HydroxideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 11116115BenzylvinyletherYield 95%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
75 °C

Procedure

45 g (0.25 equivalent) of dicyclopentadiene skeleton phenolic resin, DPP-3H (special phenolic resin manufactured by Nippon Petrochemical Co., Ltd.), 38.1 g of vinylbenzyl chloride CMS-AM (m-/p-isomers: 50/50 wt % mixture) (purity of 91%, 0.25 mol), 2.4 g of tetra-n-butylammonium bromide, 0.038 g of 2,4-dinitrophenol and 200 g of methyl ethyl ketone were charged into a 1-liter four-necked flask equipped with a thermoregulator, stirrer, cooling condenser and dropping funnel and dissolved under agitation, and 40 g of a 50 wt % aqueous solution of NaOH (NaOH purity of 95%, 0.475 mol) was added dropwise at 75° C. to the obtained solution over 20 minutes and further stirred at 75° C. for 4 hours. After the obtained reaction mixture was cooled to room temperature, it was neutralized with 2N hydrochloric acid, 100 g of toluene was added, and the organic layer was then washed three times with 300 g of distilled water. After methyl ethyl ketone was removed under reduced pressure, the reaction product was precipitated in 300 ml of methanol to collect solid matter through filtration, which was then dried at 50° C. in a vacuum oven to obtain a vinylbenzyl ether compound at a yield of 95%. This is designated as compound 3.

Workup

  1. customequipped with a thermoregulator, stirrer
  2. temperaturecooling condenser
  3. additionwas added dropwise at 75° C. to the obtained solution over 20 minutes
  4. customAfter the obtained reaction mixture
  5. temperaturewas cooled to room temperature
  6. additionwas added
  7. washthe organic layer was then washed three times with 300 g of distilled water
  8. customAfter methyl ethyl ketone was removed under reduced pressure
  9. customthe reaction product was precipitated in 300 ml of methanol
  10. customto collect solid matter
  11. filtrationthrough filtration, which
  12. customwas then dried at 50° C. in a vacuum oven

Sources & evidence

ORD record
ord-3492063a70aa4749b51545e760e75ef3
Source dataset
uspto-grants-2009_04
Patent number
US07514379B2

Reaction notes

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