ChemicalBook CAS DataBase List Isobutylbenzene

Isobutylbenzene synthesis

8synthesis methods

Product Name:Isobutylbenzene
CAS Number:538-93-2
Molecular formula:C10H14
Molecular Weight:134.22

Isobutylbenzene synthesis: Isobutyrophenone, underwent a Wolff–Kishner reduction using hydrazine hydrate and strong base conditions to synthesize isobutyl benzene. The solvent for this reaction was replaced with the more sustainable solvent glycerol. The glycerol for this reaction was obtained from the synthesis of biodiesel. The reaction was allowed to heat at reflux (149–155 °C) for a period of three hours. An average 51 % yield of isobutyl benzene was obtained from the solar synthesis, compared to a 55 % yield from an in-lab, electrical heating analysis.
synthesis of Isobutylbenzene

5674-02-2
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108-90-7
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538-93-2
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$14.00/5mL

Yield:538-93-2 92%

Reaction Conditions:

with iron(II) chloride tetrahydrate;1,3-bis[2,6-diisopropylphenyl]imidazolium chloride in tetrahydrofuran at 70; for 3 h;Inert atmosphere;

Steps:

Representative cross-coupling procedure
General procedure: 1,3-Bis-(2,6-diisopropylphenyl)imidazolium chloride (0.1 mmol, 10 mol %) was added to Vial 1 containing a stir bar which was then fitted with a septum. FeCl₂·(H₂O)₄ (9.9 mg, 0.05 mmol, 5 mol %) was added to Vial 2 containing a stir bar which was then fitted with a septum. Both Vial 1 and Vial 2 were evacuated and backfilled with argon. Chlorobenzene (102 μL, 1 mmol) was then added via syringe to Vial 2. Freshly distilled THF (10.5 mL) was added via syringe to Vial 1, and isobutylmagnesium chloride (1.5 mL of a 2 M solution in THF, 3 mmol) was added with stirring. Vial 1 was placed in an oil bath at 70 °C and stirred for 10 min. Then the contents of Vial 1 were transferred to Vial 2 via syringe, and Vial 2 was placed in the oil bath at 70 °C. After 3 h, the reaction was removed from the oil bath and allowed to cool to room temperature. The reaction mixture was poured into a separatory funnel followed by 15 mL of 1 M HCl and 15 mL of pentane. The pentane layer was washed with water (1 × 15 mL) and brine (1 × 15 mL). The pentane layer was dried over Na₂SO₄ and the solvent was removed in vacuo. The crude oil was purified by distillation resulting in a colorless oil (122 mg, 92%). ¹H NMR and GC-MS were consistent with known material.

References:

Perry, Marc C.;Gillett, Amber N.;Law, Tyler C. [Tetrahedron Letters,2012,vol. 53,# 33,p. 4436 - 4439] Location in patent:experimental part

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