Ethyl vinyl ether → 4-[2-(Ethenyloxy)ethyl]phenol

HRID 2086323Notes

Reaction equation

HRID 2086323 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[CH2:11](OC=C)[CH3:12]>C([O-])(=O)C.[Hg+]>[CH:11]([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1)=[CH2:12]

Participants

4

Reactant 2

HCID 8023Ethyl vinyl etherHCID 10393Tyrosol2×

Product 1

HCID 154965104-[2-(Ethenyloxy)ethyl]phenolYield 60%

Reagents, catalysts & solvents 1

HCID 61181Mercurous acetateCatalyst

Conditions

Temperature
0 °C

Procedure

4-Hydroxyphenethyl alcohol of formula 3a (15.0 g, 108.0 mmol) was added to ethylvinyl ether of formula 4(200 ml) and stirred for 20 minutes. After cooling to 0° C., mercury acetate (3.4 g, 10.8 mmol) was added and the reaction mixture was stirred for 24 hrs at room temperature. After evaporating solvent, the residue was purified by fresh column chromatography on silica gel (hexane/ethylacetate=5/1, v/v) to obtain pale yellow liquid of the desired product, 4-(2-vinyloxyethyl)phenol of formula 5a (11.0 g, 65 mmol, yield 60%).

Workup

  1. stirringthe reaction mixture was stirred for 24 hrs at room temperature
  2. customAfter evaporating solvent
  3. customthe residue was purified by fresh column chromatography on silica gel (hexane/ethylacetate=5/1

Sources & evidence

ORD record
ord-9221772d99e7422d96a670f9e7ad2c2e
Source dataset
uspto-grants-2004_04
Patent number
US06723798B1

Reaction notes

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