2-(2,3-DIMETHYL-PHENOXY)-2-METHYL-PROPIONIC ACID synthesis
- Product Name:2-(2,3-DIMETHYL-PHENOXY)-2-METHYL-PROPIONIC ACID
- CAS Number:667440-80-4
- Molecular formula:C12H16O3
- Molecular Weight:208.25
526-75-0
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667440-80-4
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Yield:667440-80-4 76%
Reaction Conditions:
Stage #1: 2,3-Dimethylphenol;1,1,1-trichloro-2-methyl-2-propanolwith sodium hydroxide in acetone at 0 - 20; for 49 h;
Stage #2: with hydrogenchloride;water in acetone; pH=1;
Steps:
25.A
Example 25A 2-(2,3-Dimethylphenoxy>2-methyl-propionic acid; To an ice cold solution of 2,3-dimethylphenol (136 mg, 1.0 mmol) and 1,1,1- trichloro-2-methyl-2-propanol hydrate (492 mg, 2.75 mmol) in acetone (2 mL) was added powdered sodium hydroxide (393 mg, 9.83 mmol) in three equal portions at 1 hour interval.After each addition reaction mixture was allowed to come to room temperature. Before last addition of sodium hydroxide, acetone (2 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 48 hours and concentrated in vacuo.The residue was diluted with water and acidified to pH 1 with aqueous HCl and extracted with diethyl ether (3x5 mL). The organic layers were pooled, dried (Na2SO4) and filtered.The filtrate was concentrated under reduced pressure to provide the crude that was purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (40mm X 100mm,7um particle size) using a gradient of 10% to 100% acetonitrile:0.1% aqueous TFA over12min (15min run time) at a flow rate of 70mL/min. to provide the title compound as a pale yellow solid (158 mg, 76%).
References:
WO2006/74244,2006,A2 Location in patent:Page/Page column 62
2052-01-9
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526-75-0
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667440-80-4
14 suppliers
$45.00/100mg
669738-96-9
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667440-80-4
14 suppliers
$45.00/100mg