ChemicalBook CAS DataBase List 4-ISOPROPYLBENZYL CHLORIDE

4-ISOPROPYLBENZYL CHLORIDE synthesis

12synthesis methods

Product Name:4-ISOPROPYLBENZYL CHLORIDE
CAS Number:2051-18-5
Molecular formula:C10H13Cl
Molecular Weight:168.66

122-03-2 Synthesis

122-03-2
351 suppliers
$6.00/25g

2051-18-5
112 suppliers
$16.39/1g

Yield: 84%

Reaction Conditions:

Stage #1:(4-isopropylbenzaldehyde) with sodium tetrahydroborate in tetrahydrofuran;methanol at 0 - 20;Inert atmosphere;Schlenk technique;Glovebox;
Stage #2: with thionyl chloride in dichloromethane at 5 - 20;Inert atmosphere;Schlenk technique;Glovebox;

Steps:

1-(Chloromethyl)-4-isopropylbenzene
500 ml of methanol was added dropwise by vigorous stirring over 5 h to a mixture of 148 g (1.0 mol) 4-isopropylbenzaldehyde and 37.8 g (1.0 mol) of NaBH₄ in 1000 ml of THF at 0-5 °C. This mixture was stirred overnight at room temperature and then evaporated under vacuum. The residue was acidified with 1200 ml of 2 M HC1 to pH~l, and the formed (4-isopropylphenyl)methanol was extracted with 3 x 400 ml of dichloromethane. The combined organic extract was dried over Na₂SO₄ and evaporated to dryness. To the residue dissolved in 1000 ml of dichloromethane 73 ml (1.0 mol) of thionyl chloride was added dropwise at +5°C. The resulting solution was stirred at room temperature overnight, evaporated to dryness, and then the residue was dissolved in 750 ml dichloromethane. The formed solution was washed by 250 ml of water. The organic layer was separated, the aqueous layer was extracted with 2 x 150 ml of dichloromethane. The combined organic extract was dried over a₂S0₄, passed through a short pad of silica gel 60 (40-63 μιη), and evaporated to dryness. Crude product was distilled under vacuum to give 142 g (84%) of a colorless liquid, b.p. 107-1 12 °C/15 mm Hg.

References:

BOREALIS AG;RESCONI, Luigi;VIRKKUNEN, Ville;NOUREDDINE, Ajellal;CASTRO, Pascal;IZMER, Vyatcheslav;KONONOVICH, Dmitry;VOSKOBOYNIKOV, Alexander WO2014/96282, 2014, A1 Location in patent:Page/Page column 54

536-60-7 Synthesis