p-Toluenesulfonic acid → 1-(4-Vinylphenoxy)-1-tert-butoxyethane

HRID 743922

Reaction equation

[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH2:22]>C(OCC)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:22])=[CH:3][CH:4]=1)=[CH2:7]

Participants

Conditions

Temperature: 10 °C

Procedure

12.02 g (100 mmol) of 4-hydroxystyrene, 0.09 g of p-toluenesulfonic acid and 100 ml of diethyl ether are introduced under a nitrogen atmosphere into a 250 ml three-neck flask. The mixture is cooled to between 0° and 5° C., and 11.02 g (110 mmol) of tert-butyl vinyl ether are added dropwise at this temperature over the course of 15 minutes. The mixture is then stirred at 10° C. for 2 hours. The reaction mixture is washed three times with 150 ml of 1N NaOH and three times with demineralized water. Stripping off of the solvent gives 16 g (72% of theory) of the desired product in the form of a yellow oil.

Workup

temperatureThe mixture is cooled to between 0° and 5° C.
washThe reaction mixture is washed three times with 150 ml of 1N NaOH and three times with demineralized water

Sources & evidence

ORD record: ord-2304c98036244104891982e779d77ca3
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05558978

Linked notes

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