ChemicalBook CAS DataBase List 4-Chlorophenethylalcohol

4-Chlorophenethylalcohol synthesis

11synthesis methods

Product Name:4-Chlorophenethylalcohol
CAS Number:1875-88-3
Molecular formula:C8H9ClO
Molecular Weight:156.61

1073-67-2 Synthesis

1073-67-2
298 suppliers
$7.00/5g

1875-88-3
267 suppliers
$6.00/5g

3391-10-4
137 suppliers
$40.60/10 g

Yield:1875-88-3 76 %Spectr. ，3391-10-4 13 %Spectr.

Reaction Conditions:

Stage #1:4-vinylbenzyl chloride with sodium tetrahydroborate;ethyl iodide in 1,2-dimethoxyethane at 25; for 20 h;
Stage #2: with dihydrogen peroxide;sodium hydroxide in water at 0 - 25; for 0.333333 h;Overall yield = 89 percent;Solvent;Reagent/catalyst;

Steps:

Typical procedure for hydroboration of alkenes with borane from NaBH4 and ethyl iodide using the PV method (Condition C)
General procedure: Ethyl iodide (380 mg, 2.4 mmol) and magnetic stirring bar were placed at the bottom of a test tube (15mm f × 130 mm), to which Galden HT-135 (2 mL) and Galden HT-200 (1 mL) were added slowly using a syringe in order. Subsequently, NaBH₄ (84 mg, 2.2 mmol), a solution of 4-methylstyrene (1a) (240mg, 2.0 mmol) in DME (5.0 mL) were added slowly in order, forming four layers. A rubber septum was fitted to the test tube, and a needle equipped with a balloon, which acted as a reservoir of borane gas during the reaction, was then pricked into the septum. The air in the test tube was removed by a syringe until the balloon was completely flattened. The test tube was stirred slowly for 20 h at 25 °C, taking care not to mix the layers. The reaction mixture was then cooled to 0 °C with ice while stirring. An aqueous NaOH solution (1 M, 1.35 mL) was added slowly in ten portions. Verifying that organic layer was changed to basic condition using a pH test paper, H₂O₂ solution (30%, 0.5 mL) was added slowly in two portions. After 20 min stirring, the organic layer was taken up with a glass pipette to a separating funnel, and washed with water and brine three times. The organic layer was dried over Na₂SO₄. After filtration, the solvent was evaporated. The residue was then purified by column chromatography on silica gel,eluting hexane/ethyl acetate (8:2) afforded 2-(p-tolyl)-1-ethanol (2a) (247 mg, 91%).

References:

Kawamoto, Takuji;Matsubara, Hiroshi;Ryu, Ilhyong;Sato, Aoi;Soga, Nene;Yoshiki, Tomo [Tetrahedron Letters,2021,vol. 69,art. no. 152977] Location in patent:supporting information

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