4-tert-Amylphenol synthesis

13synthesis methods

Product Name:4-tert-Amylphenol
CAS Number:80-46-6
Molecular formula:C11H16O
Molecular Weight:164.24

Benzene, 1-(1,1-dimethylpropyl)-4-(2-propen-1-yloxy)-

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80-46-6
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Yield:80-46-6 93%

Reaction Conditions:

Stage #1: 1-allyloxy-4-(1',1''-dimethylpropyl)benzenewith C₁₂H₃₇NiP₄⁽¹⁺⁾*C₂F₆NO₄S₂^(1-) in tetrahydrofuran at 20; for 0.5 h;Glovebox;Schlenk technique;Inert atmosphere;
Stage #2: with toluene-4-sulfonic acid in tetrahydrofuran; for 15 h;Glovebox;Schlenk technique;Reflux;Inert atmosphere;

Steps:

Procedure C: Catalysis

General procedure: Inside a glovebox, a flame-dried 15 mL Schlenk tube was charged with [Ni(PMe3)4H](SO2CF3)2N (1.6 mg,2.48 μmol, 1 mol-%), and dry THF was added (0.16 M, 1.5 mL) using a Schlenk line. The O-allyl ether(0.25 mmol, 1 equiv) was then added under argon counter-flow. The reaction mixture was allowed to stirat room temperature for 30 minutes. This was followed by addition of pTsOH·H2O (1 equiv) and thereaction mixture was then heated to reflux for the time specified. The reaction was quenched by additionof ethyl acetate and water followed by transfer to a separating funnel. The aqueous phase was extractedwith ethyl acetate (3 × 5 mL), and the combined organic phases were then dried over MgSO4 and dried byrotary evaporation to give the crude alcohol, which was finally purified by column chromatography onsilica gel.

References:

Kathe, Prasad M.;Berkefeld, Andreas;Fleischer, Ivana [Synlett,2021,vol. 32,# 16,p. 1629 - 1632] Location in patent:supporting information

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