ChemicalBook CAS DataBase List 3-chloro-4-methoxyphenylacetic acid

3-chloro-4-methoxyphenylacetic acid synthesis

8synthesis methods

Product Name:3-chloro-4-methoxyphenylacetic acid
CAS Number:13721-20-5
Molecular formula:C9H9ClO3
Molecular Weight:200.62

37612-52-5
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$23.00/1g

13721-20-5
61 suppliers
$60.00/100mg

Yield: 84%

Reaction Conditions:

with sodium hydroxide;lead(IV) tetraacetate in 1,4-dioxane;methanol;water;toluene

Steps:

7.2 3-(3-Chloro-4-methoxyphenyl)-5-methyl-4-[4-methylsulfonylphenyl]isoxazole
Step 2. Preparation of 3-chloro-4-methoxyphenylacetic acid. A mixture of 3-chloro-4-methoxyacetophenone from Step 1 (10.0 g. 54.2 mmol) and boron trifluoride etherate complex (26.6 mL, 0.216 mol) in 20 mL of methanol was added to a suspension of lead tetraacetate (24 g, 54.2 mmol) in 50 mL of toluene. The mixture was stirred at room temperature for 16 hours, treated with 50 mL of water. The phases were separated and the aqueous phase was washed with toluene. The toluene solution was dried over anhydrous MgSO₄, filtered and concentrated in vacuo to provide an oil which was dissolved in 40 mL of dioxane and treated with excess 2.5N sodium hydroxide solution. The solution was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was extracted with dichloromethane and the aqueous phase was acidified with concentrated HCl. The acidic solution was extracted with dichloromethane. The dichloromethane extract was dried over anhydrous MgSO₄, filtered and concentrated in vacuo to afford pure 3-chloro-4-methoxyphenylacetic acid (9.11 g, 84%) which was used directly in the next step.

References:

G. D. Searle & Co. US5859257, 1999, A