ChemicalBook CAS DataBase List 1,4-DIPHENYLBUTANE

1,4-DIPHENYLBUTANE synthesis

10synthesis methods

Product Name:1,4-DIPHENYLBUTANE
CAS Number:1083-56-3
Molecular formula:C16H18
Molecular Weight:210.31

108-86-1 Synthesis

108-86-1
516 suppliers
$10.00/5g

74-85-1
115 suppliers
$79.00/11l

1083-56-3
37 suppliers
$50.00/50mg

Yield: 87%

Reaction Conditions:

with (1,2-dimethoxyethane)dichloronickel(II);tris(bipyridine)ruthenium(II) dichloride hexahydrate;N,N,N,N,-tetramethylethylenediamine;N-ethyl-N,N-diisopropylamine in dimethyl sulfoxide at 50; under 760.051 Torr; for 24 h;Schlenk technique;Sealed tube;Irradiation;

Steps:

b) General procedure B (Condition B): synthesis of compound 3
General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)₂PF₆ (1.8 mg, 0.002 mmol, 1 mol %), NiCl₂.glyme (4.4mg, 0.02 mmol, 10 mol %), MeCN (4.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N’,N’-tetramethylethylenediamine, TMEDA(60 μL, 2 equiv.) and N,N-diisopropylethylamine, DIPEA (70 μL, 2 equiv.) were subsequently added inthis order. The mixture was then irradiated with blue LED (2 meter strip, 18 W) with ethylene balloonfor 24 hours at 25^oC (Figure S1, except without the use of oil bath). Then aliquot of the crude reaction mixture was subjected to GC analysis to determine the ratio between 2 and 3 (Figure S3). Reaction mixture deemed with acceptable ratio was added water (30 mL) and extracted with ethyl acetate (10mL) three times. Combined organic layer was successively washed with brine three times and dried over Na₂SO₄ and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield the product as a mixture of 2 and 3(which could not be separated by column chromatography).

References:

Li, Jiesheng;Luo, Yixin;Cheo, Han Wen;Lan, Yu;Wu, Jie [Chem,2019,vol. 5,# 1,p. 192 - 203] Location in patent:supporting information

591-50-4 Synthesis