2-(2-ethoxyphenyl)ethanol synthesis

6synthesis methods

Product Name:2-(2-ethoxyphenyl)ethanol
CAS Number:22545-14-8
Molecular formula:C10H14O2
Molecular Weight:166.22

75-21-8
215 suppliers
$39.10/1mL

583-19-7
98 suppliers
$15.00/5g

22545-14-8
11 suppliers
$473.00/5g

Yield:22545-14-8 65%

Reaction Conditions:

Stage #1: beta-bromophenetolewith iodine;magnesium in tetrahydrofuran at 0; for 0.5 h;Inert atmosphere;Reflux;
Stage #2: oxirane in tetrahydrofuran at 20;

Steps:

11 Synthesis of Compound 11.3.

Into a 250-mL 3-necked round-bottom flask, maintained with an inert atmosphere of nitrogen, was placed Mg (1.0 g, 41.67 mmol, 2.09 equiv) and I₂ (10 mg).
Then a solution of 1-bromo-2-ethoxybenzene (4.0 g, 19.89 mmol, 1.00 equiv) in 25 mL THF was added dropwise and the resulting mixture was heated to reflux for 0.5 hr.
After the reaction was complete, the resulting mixture was cooled to 0° C. and then oxirane (50 mL) was added in one portion.
The reaction mixture was stirred overnight at room temperature.
The reaction was then quenched by the addition of 50 mL of NH₄Cl (aq.) and extracted with 3*50 mL of ethyl acetate.
The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum.
The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10).
Purification afforded 2.14 g (65%) of 2-(2-ethoxyphenyl)ethan-1-ol as a yellow oil.
Synthesis of Compound 11.4.

References:

US2013/123231,2013,A1 Location in patent:Paragraph 0399; 0402; 0403