[ CAS No. 2088-24-6 ] {[proInfo.proName]}

Name: 2088-24-6|2-(3-Methoxyphenoxy)acetic acid|95%
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SKU: A602415
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COA NMR CNMR HPLC LC-MS

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CAS No. :	2088-24-6	MDL No. :	MFCD00014357
Formula :	C₉H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AHDPQRIYMMZJTF-UHFFFAOYSA-N
M.W :	182.17	Pubchem ID :	74969
Synonyms :

Safety of [ 2088-24-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2088-24-6 ]
Downstream synthetic route of [ 2088-24-6 ]

[ 2088-24-6 ] Synthesis Path-Upstream 1~1

1
[ 2088-24-6 ]
[ 15832-09-4 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 2, p. 104 - 106

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Yield	Reaction Conditions	Operation in experiment
88%	With toluene-4-sulfonic acid at 20℃;
	With hydrogenchloride
	With sulfuric acid In ethanol; water Reflux;

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; phosphorus trichloride at 60℃;
	With phosphorus pentachloride; phosphorus trichloride
	With thionyl chloride for 5h; Heating;

	With oxalyl dichloride In dichloromethane for 3h;	11 2-Amino-4-bromobenzonitrile was dissolved in 4: 1 AcOHZH2SO4 to form a suspension. The mixture was stirred for 4 h until it became clear and all starting material was consumed as monitored by LC-MS. The solution was poured into ice water and extracted by EtOAc three times. The combined organic layer was washed with brine and dried over Na2SO4. After filtration, the solvent was removed to provide 11-1. Substituted benzyloxy acetic acid (1.1 equiv) was treated with 2 M oxalyl chloride in DCM for 3 h and concentrated to give the corresponding acid chloride, which was then added to a stirred solution of 11-1 and pyridine (5 equiv) in DCM. The reaction mixture was stirred for 3 h until 11-1 was consumed as monitored by LC-MS. The precipitate was collected by filtration and was dried under vacuum to provide 11-2 as white solid. 11-2, potassium carbonate (4 equiv), boronic ester (1.5 equiv) and Pd(PPh3 )4( 10%) were dissolved in 4: 1 dioxane/water and sealed in a microwave tube. The reaction mixture was degassed and heated by microwave for 30min at 140 0C. The solvent was removed and the residue was subjected to preparative HPLC to provide product 11-3 as a TFA salt.
	With dmap; thionyl chloride In dichloromethane for 2h; Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃;	2-(3-Methoxyphenoxy)acetyl chloride (47b). 2-(3-Methoxyphenoxy)acetyl chloride (47b). A 500 ml_ flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with 3-methoxyphenoxyacetic acid (20.0 g, 1 10 mmol), CH2CI2 (120 ml_), and DMF (0.2 ml_). Oxalyl chloride (2M in CH2CI2, 69 ml_, 137 mmol) was added to the resultant solution over 45 min forming an orange solution. The mixture stirred overnight at rt. The solution was concentrated in vacuo to give 22.7 g of 47b as an orange oil (100%). HPLC analysis (15:10:75 H2O:A1 :MeOH) showed a purity of 93% with a retention time of 3.9 min.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;	General synthetic procedure for compounds 8-11 and 13-36 General procedure: To a stirred suspension of various carboxylic acid 4a, 4b, 6a and 8a (1.0 equiv) in CH2Cl2 (25 mL) was added oxalyl chloride (3.0 equiv) and a catalytic amount of DMF. After stirring at room temperature for 3 h, the reaction was concentrated under reduced pressure to afford a yellow oil crude acyl chloride. To a solution of methyl 2-(4-amino-2-fluorophenoxy)acetate 3a (1.0 equiv) in CH2Cl2(25 mL) was added Et3N (1.5 equiv), and this mixture was cooled to -5 °C. Subsequently, the crude acyl chloride obtained above was added in dropwise at a rate to ensure that the temperature did not exceed 0 °C. The solution was stirred for another 2 hrs at 25 °C, then washed successively with 10% HCl (2 × 25 mL), 10% NaHCO3 (2 × 25 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was then evaporated to give the impure amide which was recrystallized from ethanol to give the desired products as colorless crystals. To a solution of the obtained crystals (1.0 equiv)in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 8-11 and 13-36 as colorless crystals.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 3h;	5.1.30. General procedures for the synthesis 28a-g General procedure: To a solution of the acid (22a-g) (1.2 eq.) in DCM, oxalyl chlorideand 1 drop DMF were added dropwise at 0 C. After 3 h, DCM wasremoved by rotary evaporation. The resulting acyl chloride dissolvedin THF and pyridine was added dropwise into a solution of26 (1.0 eq.) in THF at 0 C, then slowly warmed to r.t. and continuedstirring for 5e6 h. 1 M HCl was added and extracted with ethylacetate for three times. The organic layer was combined, washedwith brine for once, dried over anhydrous Na2SO4 and concentratedto afford compounds 27a-g. To the solution of 27a-g in ethyl acetate,HCl gaswas added for 0.5 h, and the resulting solidwas filteredto obtain desired compounds 28a-g.

Yield	Reaction Conditions	Operation in experiment
	With ammonia
	Multi-step reaction with 2 steps 1: HCl 2: aqueous NH₃ / 0 °C

[ CAS No. 2088-24-6 ] {[proInfo.proName]}

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[ 2088-24-6 ] Synthesis Path-Upstream 1~1

[ 2088-24-6 ] Synthesis Path-Downstream 1~88