[ CAS No. 1711-24-6 ] {[proInfo.proName]}

Name: 1711-24-6|4-(2-Hydroxyethoxy)benzoic acid|97%
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Product Details of [ 1711-24-6 ]

CAS No. :	1711-24-6	MDL No. :	MFCD00020367
Formula :	C₉H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QLIQIXIBZLTPGQ-UHFFFAOYSA-N
M.W :	182.17	Pubchem ID :	4312254
Synonyms :

Safety of [ 1711-24-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1711-24-6 ]

* 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.

Downstream synthetic route of [ 1711-24-6 ]

[ 1711-24-6 ] Synthesis Path-Downstream 1~71

1
[ 75-21-8 ]
[ 99-76-3 ]
[ 1711-24-6 ]

Reference： [1]Patent: US2806054,1954,A

2
[ 1711-24-6 ]
[ 65136-50-7 ]

Reference： [1]Patent: DE412699,1925,C
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724

3
[ 3204-73-7 ]
[ 1711-24-6 ]

Yield	Reaction Conditions	Operation in experiment
42%		Intermediate 4; 4-(2-Hydroxy-ethoxy)-benzoic acid; 4-(2-Hydroxy-ethoxy)-benzoic acid methyl ester (400 mg, 2.04 mmol) is combined with a mixture of 1 N NaOH (3 mL)and MeOH (3 mL) and the mixture is stirred at 80 C for 1 h. The solvents are evaporated and the resulting residue is dissolved in a small amount of water and acidified with 1 N HCl. The crystals are collected, washed with water, and dried to provide 154 mg (42%) of the titled compound. NMR (DMSO-dg): δ 12.64 (br, EPO <DP n="32"/>IH), 7.90 (d, 2H, / = 8.2 Hz), 7.03 (d, 2H, J = 8.2 Hz), 4.93 (br, IH), 4.07 (t, 2H, J - 4.9 Hz), 3.75 (m, 2H).

Reference： [1]Patent: WO2006/101808,2006,A1 .Location in patent: Page/Page column 30-31
[2]Patent: DE412699,1925,C
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724

4
[ 1711-24-6 ]
[ 108-24-7 ]
[ 52404-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 16h;	4-(2-hydroxyethoxyl)benzoic acid (424 mg, 2.33 mmol) and 1.3 ml of triethylamine were dissolved in 10 ml of methylene chloride Four equivalents of acetic anhydride were added, and the mixture was stirred for 16 hours at room temperature. The solvents and excess triethyl amine was then removed by rotary evaporation, and the residue was partitioned between 5 ml each of methylene chloride and water. The 2-phase mixture was acidified to pH 2.0, the layers were separated, and the aqueous layer was extracted twice with 5 ml portions of methylene chloride. The solvent was removed under reduced pressure from the combined organic layers, and the product used as is for the next step.

Reference： [1]Patent: US2806054,1954,A
[2]Patent: US2015/202332,2015,A1 .Location in patent: Paragraph 0072

5
[ 79-41-4 ]
[ 1711-24-6 ]
[ 69260-39-5 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 477 - 482

6
[ 1711-24-6 ]
[ 51009-27-9 ]
[ 96718-98-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 83 - 97

7
[ 1711-24-6 ]
[ 79-10-7 ]
[ 69260-38-4 ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 452 - 453
[2]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 155,p. 113 - 128
[3]Molecular Crystals and Liquid Crystals,2016,vol. 624,p. 1 - 10

8
[ 107-07-3 ]
[ 99-96-7 ]
[ 1711-24-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium iodide; sodium hydroxide; In ethanol; water; at 70℃; for 24h;	Add 10.00 g (0.25 mol) of NaOH and 50 mL of water to a three-necked flask.100mL of ethanol, after all the NaOH is dissolved,Add 13.80 g (0.1 mol) of p-hydroxybenzoic acid,Add a little KI to the flask and warm to 70 C.Chloroethanol9.66g (0.12 mol),Constant temperature reaction for 24 h.After the reaction is completed, distilled water is added, and concentrated hydrochloric acid is added dropwise to pH=5.Filtered to a white solid and recrystallized from water.White needle crystal 4-hydroxyethoxybenzoic acid,The yield was 85%.

Reference： [1]Patent: CN103922937,2016,B .Location in patent: Paragraph 0028; 0030; 0040; 0042
[2]Chemistry Letters,2007,vol. 36,p. 452 - 453
[3]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 477 - 482
[4]Molecular Crystals and Liquid Crystals,2016,vol. 624,p. 1 - 10

9
[ 540-51-2 ]
[ 99-96-7 ]
[ 1711-24-6 ]

Reference： [1]Journal of Materials Chemistry A,2015,vol. 3,p. 10738 - 10746
[2]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 155,p. 113 - 128

11
[ 874483-75-7 ]
[ 1711-24-6 ]
[ 65136-50-7 ]

Reference： [1]Patent: DE412699,1925,C
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724

12
[ 1892-43-9 ]
[ 124-38-9 ]
[ 1711-24-6 ]

Reference： [1]Journal of Organometallic Chemistry,1999,vol. 590,p. 63 - 70

13
[ 124-38-9 ]
[ 34743-88-9 ]
[ 1711-24-6 ]

Reference： [1]Journal of Organometallic Chemistry,1999,vol. 590,p. 63 - 70

14
[ 1003578-77-5 ]
[ 1711-24-6 ]
N-(2-(4-(2-hydroxyethoxy)benzamido)ethyl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With N-ethyl-N,N-diisopropylamine; HATU; In tetrahydrofuran; at 18 - 25℃;	N- (2-Aminoethyl) -l-phenyl-3- (trifluoromethyl) -lH-pyrazole- 4-carboxamide hydrochloride (0.20 g, 0.60 itimol), 4- (2- hydroxyethoxy) benzoic acid (0.11 g, 0.60 mmol), and HATU (0.27 g, 0.72 mmol) were suspended in THF (10 mL) . DIPEA (0.34 ml, 2.0 mmol) was added and the mixture was stirred at room temperature overnight. The solution was quenched with water (75 mL) and the solid was collected by filtration and dried to provide N- (2- (4- (2-hydroxyethoxy) benzamido) ethyl) -l-phenyl-3- (trifluoromethyl) -lH-pyrazole-4-carboxamide (0.152 g, 55% yield): 1H NMR (400 MHz, DMSO-d6) δ 3.41 (br, 4H), 3.71 - 3.72 (m, 2H), 4.00 - 4.05 (m, 2H), 4.90 (t, J = 5.2 Hz, IH), 6.99 (d, J = 7.6 Hz, 2H), 7.45 - 7.50 (m, IH), 7.61 (t, J = 7.6 Hz, 2H), 7.80 - 7.83 (m, 4H), 8.46 - 8.50 (m, 2H), 9.07 (s, IH); m/z (APCI pos) 463.0 (100%) (M+H) .

Reference： [1]Patent: WO2008/11131,2008,A2 .Location in patent: Page/Page column 230-231

15
[ 1711-24-6 ]
[ 133945-18-3 ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 452 - 453
[2]Journal of Materials Chemistry A,2015,vol. 3,p. 10738 - 10746

16
[ 1711-24-6 ]
[ 68540-08-9 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 477 - 482

17
[ 1711-24-6 ]
4-[2-(2-Methyl-acryloyloxy)-ethoxy]-benzoic acid 4-p-tolylazo-phenyl ester [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 477 - 482

18
[ 1711-24-6 ]
4-[2-(2-Methyl-acryloyloxy)-ethoxy]-benzoic acid 4-(4-nitro-phenylazo)-phenyl ester [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1993,vol. 237,p. 477 - 482

19
[ 1711-24-6 ]
[ 91598-49-1 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 155,p. 113 - 128
[2]Patent: CN103922937,2016,B

20
[ 1711-24-6 ]
4-(2-Acryloyloxy-ethoxy)-benzoic acid 4-[2-(4-cyano-phenyl)-ethyl]-phenyl ester [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 155,p. 113 - 128

21
[ 1711-24-6 ]
[ 65136-51-8 ]

Reference： [1]Patent: DE412699,1925,C
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724
[2]Patent: DE412699,1925,C
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724

22
[ 1711-24-6 ]
4-(2-iodo-ethoxy)-benzoic acid [ No CAS ]

23
[ 1711-24-6 ]
4-(2-iodo-ethoxy)-benzoic acid methyl ester [ No CAS ]

24
[ 1711-24-6 ]
[ 99854-16-7 ]

Reference： [1]Patent: US2806054,1954,A

25
[ 1711-24-6 ]
4-(2-chloro-ethoxy)-benzoic acid benzyl ester [ No CAS ]

26
[ 1711-24-6 ]
4-(2-iodo-ethoxy)-benzoic acid benzyl ester [ No CAS ]

27
[ 99-76-3 ]
[ 1711-24-6 ]

Reference： [1]Patent: DE412699,1925,C
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 15,p. 1724

28
[ 120-47-8 ]
[ 540-51-2 ]
[ 1711-24-6 ]

Yield	Reaction Conditions	Operation in experiment
		In accordance with Scheme 1 below, an acrylic compound having an oxetanyl group (acrylic compound 1) was synthesized using 3-ethyl-3-hydroxymethyloxetane (OXT-101, manufactured by Toagosei Co., Ltd.). The 1H-NMR spectrum of the acrylic compound 1 is shown in Fig. 1. "x" in the figures indicates the peak of the impurities.

Reference： [1]Patent: EP1405850,2004,A1 .Location in patent: Page 8; 13-14

29
[ 1711-24-6 ]
[ 814-68-6 ]
[ 69260-38-4 ]

Yield	Reaction Conditions	Operation in experiment
76.3%	With triethylamine; In tetrahydrofuran; at 20℃; for 26h;Cooling with ice;	Add in three-necked flasks4-hydroxyethoxybenzoic acid5.46g (0.03mol),100 mL of tetrahydrofuran and 3.3 g of triethylamine (0.033 mol),A mixed solution of acryloyl chloride and tetrahydrofuran was added dropwise in an ice water bath, and added dropwise for 2 hours.Then react at room temperature for 24 h, filter, distill off most of the tetrahydrofuran, add a small amount of water,A large amount of white precipitate was precipitated, washed three times with warm water, and dried.4-(2-acryloyloxyethoxy)benzoic acid,The yield was 76.3%.
	With dmap; In tetrahydrofuran;	[Reference Example 5 (synthesis of acrylic compound 5)]; In accordance with Scheme 5 below, an acrylic compound 5 was synthesized. [Show Image]; [Reference Example 6 (synthesis of acrylic compound 6)]; In accordance with Scheme 6 below, an acrylic compound 6 was synthesized. [Show Image]
	With dmap; 2,6-di-tert-butyl-4-methyl-phenol; In tetrahydrofuran; at 60℃; for 2h;	In accordance with Scheme 1 below, an acrylic compound having an oxetanyl group (acrylic compound 1) was synthesized using 3-ethyl-3-hydroxymethyloxetane (OXT-101, manufactured by Toagosei Co., Ltd.). The 1H-NMR spectrum of the acrylic compound 1 is shown in Fig. 1. "x" in the figures indicates the peak of the impurities.

Reference： [1]Patent: CN103922937,2016,B .Location in patent: Paragraph 0028; 0031; 0040; 0044
[2]Patent: EP1990339,2008,A1 .Location in patent: Page/Page column 14-15
[3]Patent: EP1405850,2004,A1 .Location in patent: Page 8; 13-14
[4]Journal of Materials Chemistry A,2015,vol. 3,p. 10738 - 10746

30
[ 1711-24-6 ]
[ 51207-66-0 ]
[4-(2-hydroxy-ethoxy)-phenyl]-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 72h;	Example 12; [4-(2-Hydroxy-ethoxy)-phenyl]-(2-(S)-pyrrolidin-l-ylmethyl-pyrrolidin-l-yl)- methanone; 4-(2-Hydroxy-ethoxy)-benzoic acid (152 mg, 0.84mmol), (S)(+)-l-(2- pyrrolidinylmethyl)pyrrolidine (193 mg, 1.25 mmol) and triethylamine (303 mg, 3.0 mmol) are dissolved in dichloromethane (5.0 mL) and benzotriazol-1- yloxytris(pyrrolidino)phosphoniurn hexafluorophosphate (PyBOP) (786 mg, 1.5 mmol) is added to the mixture. The mixture is stirred at room temperature for 3 days. The reaction mixture is diluted with dichloromethane, washed with brine, dried over Na2SU4, filtered and evaporated. The crude product is purified using silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH = 20:1) to give 177 mg (66%) of the title compound.Observed Mass 319.

Reference： [1]Patent: WO2006/101808,2006,A1 .Location in patent: Page/Page column 40

31
1N-HCl [ No CAS ]
aqueous sodium chloride [ No CAS ]
[ 2177-18-6 ]
[ 144-55-8 ]
[ 150-76-5 ]
[ 78-93-3 ]
[ 652-67-5 ]
[ 1711-24-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	lipase; In tetrahydrofuran; hexane; dichloromethane;	Next, after dissolving 18.2 parts of 4-(2-hydroxyethoxy)benzoic acid thus obtained in 300 ml of THF, 19.5 parts of vinyl acrylate, 18 parts of lipase PS, and a small amount of p-methoxyphenol were added to the solution followed by stirring for 3 hours at 40C. After filtrating off lipase PS from the reaction mixture obtained, the filtrate was distilled under reduced pressure and solid residue formed was recrystallized from a 2/1 mixed solution of 2-butanone/hexane to obtain 17.5 parts (yield 74%) of (4-(2-propenoyloxyethoxybenzoic acid. On the other hand, after dissolving 10.0 parts of isosorbide by stirring together with 0.5 part of p-toluenesulfonic acid·hydrate and 100 ml of THF at room temperature, 5.76 parts of DHP diluted with 50 ml of THF was added dropwise to the solution over a period of 90 minutes, and then the mixture was stirred for 90 minutes at room temperature. Then, the solvent was distilled off from the reaction mixture obtained, the residue formed was dissolved in 250 ml of methylene chloride, and the solution was successively washed with 150 ml of a saturated aqueous sodium chloride solution, 150 ml of an aqueous solution of 1N-HCl, 150 ml of a saturated aqueous sodium chloride solution, 150 ml of a saturated aqueous sodium hydrogencarbonate solution, and 150 ml of a saturated aqueous sodium chloride solution.

Reference： [1]Patent: EP980868,2000,A1

32
[ 1711-24-6 ]
[ 56-35-9 ]
[ 40585-52-2 ]

Reference： [1]Patent: JP72-49054,1972,
C.A.,1973,vol. 78,p. 124715
[2]Patent: JP72-49054,1972,
C.A.,1973,vol. 78,p. 124715
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.4.6.2, page 181 - 191
[4]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.4.6.2, page 181 - 191

33
[ 25389-23-5 ]
[ 1711-24-6 ]

Yield	Reaction Conditions	Operation in experiment
		[Reference Example 5 (synthesis of acrylic compound 5)]; In accordance with Scheme 5 below, an acrylic compound 5 was synthesized. [Show Image]; [Reference Example 6 (synthesis of acrylic compound 6)]; In accordance with Scheme 6 below, an acrylic compound 6 was synthesized. [Show Image]

Reference： [1]Patent: EP1990339,2008,A1 .Location in patent: Page/Page column 14-15

34
[ 533-58-4 ]
[ 1711-24-6 ]
[ 1200959-80-3 ]

Reference： [1]Synthesis,2009,p. 3311 - 3321

35
[ 1711-24-6 ]
[ 102541-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Rh/Al2O3; In tetrahydrofuran; ethanol; at 50 - 60℃; under 37503.8 - 60006 Torr; for 60h;	Example 1A4-(2-Hydroxyethoxy)cyclohexanecarboxylic acid; 1.00 g (5.49 mmol) of <strong>[1711-24-6]4-(2-hydroxyethoxy)benzoic acid</strong> is dissolved in 30 ml of dry THF and 30 ml of dry ethanol, and 1.13 mg (0.55 mmol) of rhodium on alumina are added. The reaction mixture is hydrogenated at +50 C. at a hydrogen pressure of 50 bar for 12 h. The mixture is then hydrogenated at +60 C. at a hydrogen pressure of 80 bar for a further 48 h. After filtration, the filtrate is concentrated on a rotary evaporator. The residue is directly used in the next reaction without further purification.Yield: 1.00 g (84% of theory, 87% pure)1H-NMR (400 MHz, DMSO-d6): δ=12.3 (br. s, 1H), 4.52 (br. s, 1H), 3.49-3.34 (m, 4H), 3.25-3.14 (m, 1H), 2.32-2.22 (m, 1H), 2.20-0.90 (m, 8H).GC-MS (Method 8): Rt=1.43 min; MS (ESIpos): m/z=222 [M+H]+.

Reference： [1]Patent: US2010/22544,2010,A1 .Location in patent: Page/Page column 15

36
2-(4-(hydroxymethyl)phenoxy)ethanol [ No CAS ]
[ 1711-24-6 ]
[ 22042-73-5 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 16299 - 16301

37
[ 1711-24-6 ]
C₂₇H₄₅NO₂Si [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1358 - 1361

38
[ 1711-24-6 ]
C₂₄H₃₇NO₂ [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1358 - 1361

39
[ 1711-24-6 ]
C₄₆H₆₈N₂O₆ [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1358 - 1361

40
[ 1711-24-6 ]
[ 1265966-33-3 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1358 - 1361

41
[ 1711-24-6 ]
C₂₂H₃₆INO₂ [ No CAS ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1358 - 1361

42
[ 107-21-1 ]
[ 99-96-7 ]
[ 1711-24-6 ]