[ CAS No. 13205-46-4 ] {[proInfo.proName]}

Name: 13205-46-4|4-Isopropoxybenzoic acid|98%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 13205-46-4 ]

CAS No. :	13205-46-4	MDL No. :	MFCD00044318
Formula :	C₁₀H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZVERWTXKKWSSHH-UHFFFAOYSA-N
M.W :	180.20	Pubchem ID :	72972
Synonyms :

Safety of [ 13205-46-4 ]

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

Application In Synthesis of [ 13205-46-4 ]

* 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 [ 13205-46-4 ]
Downstream synthetic route of [ 13205-46-4 ]

[ 13205-46-4 ] Synthesis Path-Upstream 1~3

1
[ 13205-46-4 ]
[ 82657-71-4 ]

Reference： [1] Patent: EP1223170, 2002, A1,

2
[ 13205-46-4 ]
[ 213598-07-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-chloro-succinimide In N,N-dimethyl-formamide	[00177] To a solution of 4-isopropoxylbenzoic acid 1.1 (25 g, 140 mmol) in DMF(15OmL) was added NCS (24 g, 182 mmol). The reaction mixture was stirred overnight. H₂O (50OmL) was added to the reaction mixture, and the precipitate was collected, washed with water, and dried in vacuo to give 1.2 (26.4 g, 88 percent) as a white solid, which was used in the next step without further purification. LRMS (M+H⁺) m/z 213.0.
88%	With N-chloro-succinimide In N,N-dimethyl-formamide	To a solution of 4-isopropoxylbenzoic acid 3.1 (25 g, 140 mmol) in DMF ( 150 mL) was added NCS (24 g, 182 mmol). The reaction mixture was stirred overnight. H₂O (500 mL) was added to the reaction mixture. The precipitate was collected, washed with water and <n="55"/>dried to give 3.2 (26.4 g, 88 percent) as a white solid, which was used in the next step without further purification.

Reference： [1] Patent: WO2007/56056, 2007, A2, . Location in patent: Page/Page column 51
[2] Patent: WO2007/56143, 2007, A2, . Location in patent: Page/Page column 53-54
[3] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

3
[ 13205-46-4 ]
[ 1088965-37-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[2] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[3] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[4] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[5] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263
[6] Organic Process Research and Development, 2010, vol. 14, # 5, p. 1254 - 1263

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Yield	Reaction Conditions	Operation in experiment
94%	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;	1D Specifically, to a stirred mixture of 4-isopropoxy-benzoic acid (10.0 g, 55.5 mmol) and DMF (1 drop) in methylene chloride (80 mL) was added dropwise over a period of 15 min a solution of oxalyl chloride (7.40 g, 58.2 mmol) in methylene chloride (20 mL). After stirring for 2.45 h at ambient temperature the reaction mixture was concentrated, taken up into a small amount of methylene chloride, filtered to remove insolubles and again concentrated to afford 8 (10.38 g, 94%) as a yellow liquid: 1H NMR (300 MHz, CDCI3) δ 8.05 (d, 2H), 6.94 (d, 2H), 4.68 (m, 1H)1 1.44 (d, 6H).
	With thionyl chloride
	With phosphorus(V) chloride

	With thionyl chloride In benzene for 11h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 0.666667h;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
	With oxalyl dichloride; N,N-dimethyl-formamide at 20℃; for 1h;
	With thionyl chloride Reflux;	5.1.18. General procedure 2 for preparation of 64-81, 83-91 General procedure: To a solution of organic acids (1.1 eq) in SOCl2, the reaction wasstirred at reflux, then finished, SOCl2 was removed and 5 mL THFwas added and dropwise to compound 26 (1.0 eq). Mixture wasstirred at r.t overnight. Then solvent was removed, H2O and ethylacetate was added, organic layer was dried by anhydrous Na2SO4and concentrated. Next, to a solution of compounds gained above inethyl acetate, HCl gas was added for 0.5 h, filtered the solid to affordproducts.
	With thionyl chloride at 0℃; for 24h; Reflux;	8.1.2.2. Method B, synthesis of amide bond using thionyl chloride. General procedure: The appropriate carboxylic acid (1 eq.) was cooled to 0 C and then thionyl chloride (2 eq.) was added dropwise. The mixture was thenheated under reflux for 2 h, and the excess of thionyl chloride wasevaporated under vacuum. The acid chloride was dissolved in dryTHF and added dropwise to a solution of the appropriate amine (0.9eq.) and DIPEA (3 eq.) in THF. After completion, the reactionmixture was diluted with ethyl acetate and washed with a saturatedaqueous solution of ammonium chloride and brine. Theorganic layerwas dried over anhydrous sodium sulfate, filtered, andconcentrated in vacuo. The residue was purified using columnchromatography (chloroform/methanol as eluents). The yieldswere around 50-70%.
	With sulfuryl dichloride Reflux;
	With thionyl chloride Reflux;

Yield	Reaction Conditions	Operation in experiment
82%	With nitric acid; acetic anhydride at 20℃; for 16h;	220 Reference Example 220; 4- [ (1-METHYLETHYL) oxy] -3-nitrobenzoic acid To a solution of 4- [ (1-METHYLETHYL) oxy] benzoic acid (5.41 g) in acetic anhydride. (35 mL) was added concentrated nitric acid (5.0 mL) at 0°C and the mixture was stirred at room temperature for 16 hrs. The reaction mixture was poured into ice water. The precipitates were collected by filtration and dried to give the title compound as a pale yellow powder (5.51 g, yield 82%). H NMR (200 MHz, CDC13) B ppm : 1.45 (d, J = 5.9 Hz, 6 H), 4.71 - 4. 91 (m, 1 H), 7.14 (d, J = 9.2 Hz, 1 H), 8.23 (dd, J = 8.8, 2.2 Hz, 1 H), 8.51 (d, J = 1.8 Hz, 1 H).
	With nitric acid; acetic acid

Yield	Reaction Conditions	Operation in experiment
70%	With lithium hydroxide monohydrate; water In methanol at 40℃; for 12h; Inert atmosphere;	39.2 Step 2 Compound 39-2 (166 mg, 0.797 mmol), lithium hydroxide monohydrate (50.2 mg, 1.20 mmol) were dissolved in methanol (3 mL) and water (1 mL). The mixture was stirred at 40° C. for 12 hours under nitrogen atmosphere. The mixture was added with 1M hydrochloric acid (1.2 mL). The mixture was concentrated under reduced pressure to gain solid. Then, a mixture of 20 mL/20 mL chloroform and methanol was added. The mixture was stirred for 0.5 hour and filtered. The filtrate was concentrated by a rotary evaporator and dried in vacuum to obtain compound 39-3 (144 mg, pale yellow solid) yield: 70%. (0453) 1H NMR: (400 MHz, Methonal-d4) δ 7.95 (d, J=8.8 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.74-4.66 (m, 1H), 1.35-1.29 (d, J=6.0 Hz, 6H).
	With sodium hydroxide
	With potassium hydroxide

[ CAS No. 13205-46-4 ] {[proInfo.proName]}

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[ 13205-46-4 ] Synthesis Path-Upstream 1~3

[ 13205-46-4 ] Synthesis Path-Downstream 1~88