ChemicalBook CAS DataBase List O-ALLYLANISOLE

O-ALLYLANISOLE synthesis

11synthesis methods

Product Name:O-ALLYLANISOLE
CAS Number:3698-28-0
Molecular formula:C10H12O
Molecular Weight:148.2

591-87-7 Synthesis

591-87-7
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$10.00/10g

578-57-4
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$6.00/10g

3698-28-0
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$121.00/5g

Yield:3698-28-0 95%

Reaction Conditions:

Stage #1: 2-bromoanisolewith magnesium;lithium chloride in tetrahydrofuran at 20;Inert atmosphere;
Stage #2: with iron(III)-acetylacetonate in tetrahydrofuran at 0; for 0.0833333 h;
Stage #3: Allyl acetate in tetrahydrofuran; for 2 h;

Steps:

1 Coupling of Allyl Acetate with 2-methoxyphenylmagnesium Bromide

Example 1
Coupling of Allyl Acetate with 2-methoxyphenylmagnesium Bromide
Under protective gas, 63 mg of magnesium turnings, 126 mg of anhydrous lithium chloride, 4 ml of dry tetrahydrofuran and 2.4 mmol of 2-bromoanisole were reacted at room temperature to give the Grignard compound.Then the dark-colored solution formed was cooled to 0° C. and a solution of 35.3 mg of iron(III) acetylacetonate (5 mol %) in 2 ml of dry tetrahydrofuran was added and the mixture was stirred for five minutes. Then 2 mmol of allyl acetate were added dropwise and the reaction mixture was stirred for 2 h. For workup, hydrolysis was effected with 5 ml of saturated sodium hydrogencarbonate solution and the mixture was extracted three times with 10 ml each time of ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated and purified by column chromatography on silica gel (eluent: cyclohexane-ethyl acetate). 95% of theory of 2-allylanisole was isolated.

References:

US2013/184485,2013,A1 Location in patent:Paragraph 0062; 0063