[ CAS No. 70069-04-4 ] {[proInfo.proName]}

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Quality Control of [ 70069-04-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 70069-04-4 ]

Product Details of [ 70069-04-4 ]

CAS No. :	70069-04-4	MDL No. :	MFCD00188046
Formula :	C₁₃H₂₆O₇	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HFRGASADQCZXHH-UHFFFAOYSA-N
M.W :	294.34	Pubchem ID :	3611393
Synonyms :

Safety of [ 70069-04-4 ]

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

Application In Synthesis of [ 70069-04-4 ]

* 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.

Downstream synthetic route of [ 70069-04-4 ]

[ 70069-04-4 ] Synthesis Path-Downstream 1~25

1
[ 84812-04-4 ]
[ 70069-04-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With perchloric acid In ethanol at 80℃; for 24h;
48.1%	In methanol; water for 24h; Heating;

Reference： [1]Ikeda, Isao; Emura, Hiroshi; Okahara, Mitsuo [Synthesis, 1984, # 1, p. 73 - 74]
[2]Jungk, Steven John; Moore, Jane Ann; Gandour, Richard David [Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1116 - 1120]

2
[ 76377-04-3 ]
[ 70069-04-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen In ethanol for 48h; Ambient temperature;
94%	With palladium on activated charcoal; hydrogen In ethanol for 4h; Ambient temperature;
	hydrogenolysis;

	With hydrogen; toluene-4-sulfonic acid at 25℃; Yield given;
1.74 g	With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; for 48h;	General Procedure for the Synthesis of 18-C-6 Lariat Ethers 1d-7d General procedure: To a dry round-bottom flask was added 10% (w/w) of 5% Pd/C and anhydrous EtOH (200 mL) was added to the reaction flask. The solution was degassed by bubbling the H2 gas through it twice. Benzylated lariat ethers 1c-7c (approx. 3.5 g) dissolved in anhydrous EtOH (20 mL) was added into the reaction flask. The solution was degassed twice. The reaction mixture was stirred for 48 h under 1.013 bar of hydrogen. TLC with alumina platesusing 4% 2-PrOH-CH2Cl2 as the eluent indicated the formationof product (Rf = 0.15). The product mixture was filtered and concentrated. The crude reaction mixture was then stirred into KOH aq (1 M, 50 mL) for 5 min. After this time, the impurities were removed by extraction using EtOAc until TLC showed the absence of any impurity (usually three extractions). The H2O layer was then extracted with CH2Cl2 (3 × 20 mL, monitored by alumina TLC; 4% 2-PrOH-CH2Cl2 eluent). The organic layer was collected, the solvent was removed in vacuo, and the resulting material was passed through a small plug of neutral alumina (10% MeOH-EtOAc as eluent) to furnish noncomplexed lariat products. 2-Hydroxymethyl-18-C-6 (1d)2a-gObtained in 65% yield (1.74 g) as a colorless viscous oil. 1H NMR(400 MHz, CDCl3): δ = 2.93 (s, 1 H, OH), 3.46-3.82 (m, 25 H, 12 ×CH2 and 1 × CH). 13C NMR (100 MHz, CDCl3): δ = 63.0 (CH2OH),69.6 (CH2O), 70.6 (CH2O), 70.7 (CH2O), 70.75 (2 × CH2O), 70.8(CH2O), 70.83 (CH2O), 71.0 (CH2O), 71.03 (CH2O), 71.2 (CH2O),71.8 (CH2O), 79.4 (CH). ESI-HRMS: m/z [M + H] calcd forC13H26O7: 295.1757; found: 295.1751.

Reference： [1]Fukunishi, Koji; Czech, Bronislaw; Regen, Steven L. [Journal of Organic Chemistry, 1981, vol. 46, # 6, p. 1218 - 1221]
[2]Weber, Edwin [Liebigs Annalen der Chemie, 1983, # 5, p. 770 - 801]
[3]Ctech, Bronislav [Tetrahedron Letters, 1980, vol. 21, p. 4197 - 4198]
[4]Belohradsky, Martin; Stibor, Ivan; Holy, Petr; Zavada, Jiri [Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 10, p. 2500 - 2507]
[5]Jana, Susovan; Suresh, Vallabh; Lepore, Salvatore D. [Synlett, 2015, vol. 26, # 14, p. 1977 - 1980]

3
[ 112-92-5 ]
[ 51760-23-7 ]
[ 70069-04-4 ]
2-(3-Bromo-5-octadecyloxymethyl-benzyloxymethyl)-1,4,7,10,13,16-hexaoxa-cyclooctadecane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 9820 - 9825

4
[ 70069-04-4 ]
[ 99725-12-9 ]
2-(5-Bromo-2-fluoro-benzyloxymethyl)-1,4,7,10,13,16-hexaoxa-cyclooctadecane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 9820 - 9825

5
[ 70069-04-4 ]
[ 920-46-7 ]
[ 110068-19-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: 2-hydroxymethyl-18-crown-6 With triethylamine In dichloromethane at 0℃; Stage #2: Methacryloyl chloride In dichloromethane at 0 - 20℃;	7.1 1. Preparation of 18-crown-6-methacrylate 1. Preparation of 18-crown-6-methacrylate [0211] 2-hydroxymethyl-18-crown-6 (1 mmol) was dissolved in degased CH2Cl2 (10 mL) in a Schlenk tube equipped with magnetic stirrer. The content of the flask was cooled to 0° C. and triethylamine (3 mmol) was added. The solution was stirred and then methacryloyl chloride (3 mmol) was added dropwise to the solution. The stirring was continued 2H at 0° C. and then overnight at room temperature. The reaction mixture was extracted with 1M HCl solution, washed with water then saturated Na2CO3 solution and dried over MgSO4. After filtration and evaporation of solvent, the residue was purified by chromatography on silica gel (CHCl3/MeOH 9/1 eluent) to obtain 194 mg (yield 54%) of 2-methylmethacrylate-18-crown-6. 1H NMR (300 MHz, CDCl3): 6.11 (s, 1H, ═CH2), 5.57 (s, 1H, ═CH2), 4.32-4.15 (m, 2H, CH2-OCO), 3.81-3.68 (m, 23H, CH2-O), 1.95 (s, 3H, CH3)
54%	Stage #1: 2-hydroxymethyl-18-crown-6 With triethylamine In dichloromethane at 0℃; Stage #2: Methacryloyl chloride In dichloromethane at 0 - 20℃;	8.1 1. Preparation of 18-crown-6-methacrylate [0280] 1. Preparation of 18-crown-6-methacrylate [0281] 2-hydroxymethyl-18-crown-6 (1 mmol) was dissolved in degased CH2Cl2 (10 mL) in a Schlenk tube equipped with magnetic stirrer. The content of the flask was cooled to 0° C. and triethylamine (3 mmol) was added. The solution was stirred and then methacryloyl chloride (3 mmol) was added dropwise to the solution. The stirring was continued 2H at 0° C. and then overnight at room temperature. The reaction mixture was extracted with 1M HCl solution, washed with water then saturated Na2CO3 solution and dried over MgSO4. After filtration and evaporation of solvent, the residue was purified by chromatography on silica gel (CHCl3/MeOH 9/1 eluent) to obtain 194 mg (yield 54%) of 2-methylmethacrylate-18-crown-6. 1H NMR (300 MHz, CDCl3): 6.11 (s, 1H, ═CH2), 5.57 (s, 1H, ═CH2), 4.32-4.15 (m, 2H, CH2-OCO), 3.81-3.68 (m, 23H, CH2-O), 1.95 (s, 3H, CH3)
	With triethylamine In dichloromethane at 4 - 20℃;

Reference： [1]Current Patent Assignee: PARIS CITE UNIVERSITY - US2013/344160, 2013, A1 Location in patent: Paragraph 0210; 0211
[2]Current Patent Assignee: PARIS CITE UNIVERSITY - US2013/344159, 2013, A1 Location in patent: Paragraph 0280; 0281
[3]Mayes, Andrew G.; Blyth, Jeff; Millington, Roger B.; Lowe, Christopher R. [Analytical Chemistry, 2002, vol. 74, # 15, p. 3649 - 3657]

6
[ 70069-04-4 ]
[ 106-95-6 ]
[ 84812-04-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium hydroxide In tetrahydrofuran for 2h; Heating;

Reference： [1]Buschbeck, Roy; Lang, Heinrich [Journal of Organometallic Chemistry, 2005, vol. 690, # 3, p. 696 - 703]

7
[ 2491-06-7 ]
[ 70069-04-4 ]
2-[(2-(N,N-dimethylamino)acetoxy)methyl]-1,4,7,10,13,16-hexaoxacyclooctadecane [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 1252 - 1255

8
[ 4422-95-1 ]
[ 70069-04-4 ]
[ 677736-50-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 1,3,5-benzene tris(carbonyl chloride); 2-hydroxymethyl-18-crown-6 With triethylamine In dichloromethane for 12h; Heating / reflux; Stage #2: With water In dichloromethane for 1h; Heating / reflux;	1 To a stirred solution of 18-crown-6-methanol (47 μL, 0.150 mmol), triethylamine (25 μL, 0.179 mmol), and dichloromethane (4.5 mL) was added 1,3,5-benzenetricarbonyl trichloride (20.4 mg, 0.077 mmol). The mixture was heated to reflux for 12 h, and then H2O (1.5 mL) was added and the mixture was again heated to reflux for 1 h. The solvent was removed under reduced pressure, the residue dissolved in a minimal amount of dichloromethane (500 mL), and the undesired salts were precipitated out of solution with the addition of ether (5 mL). Filtration through celite and removal of solvent under reduced pressure yielded compound 2 (54.2 mg, 0.071 mmol, 95% yield) in sufficient purity for experimental use.

Reference： [1]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - US2005/10059, 2005, A1 Location in patent: Page/Page column 6

9
[ 213599-38-3 ]
[ 70069-04-4 ]
[ 558439-79-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	In tetrahydrofuran at 20 - 30℃; for 48h;	2.2 8.13 g of compound (XXII) synthesized above, i.e. 40 mmol, are dissolved in 80 ml of anhydrous tetrahydrofuran. 40 mmol of 2-(hydroxymethyl)-18-crown-6 (Aldrich reference 38 440-0, C13H26O7, MR=294.35), i.e. 11.77 g, dissolved beforehand in 110 ml of tetrahydrofuran, are added and the reaction mas stirred at between 20 and 30° C. for 48 hours. The medium is subsequently brought to dryness by evaporation under vacuum on a water bath at 40° C. to constant weight. The yield is quantitative. 20 g of compound (Xb) are obtained. It is used as is in the following stage.

Reference： [1]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - US2005/143587, 2005, A1 Location in patent: Page/Page column 12

10
[ 70069-04-4 ]
[ 83883-26-5 ]
[ 1143623-75-9 ]

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 2414 - 2425

11
[ 70069-04-4 ]
[ 78831-37-5 ]
[ 677736-49-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: With n-butyllithium; diethylamine In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: 2-hydroxymethyl-18-crown-6 In tetrahydrofuran at -78℃; Stage #3: 2,9-bis-(bromomethyl)-1,10-phenantroline In tetrahydrofuran; dichloromethane for 24h;	1 Example 1, Compound Synthesis To a stirred solution of diethylamine (13 μL, 0.123 mmol) in THF (500 μL) at 0° C. was added nBuLi (60 μL, 2.1 M, 0.126 mmol) dropwise. The mixture was stirred for 10 min and then transferred via syringe to a solution of 18-crown-6-methanol (30 μL, 0.109 mmol) in THF (500 μL) stirred at 78° C. The solvent was removed under reduced pressure as the reaction warmed to room temperature. Excess diethylamine was removed by two consecutive additions of THF (1 mL) and removal under reduced pressure. The residue was then redissolved in THF (1 mL) and 2,9-bis(bromomethyl)-1,10-phenanthroline (Chandler et al. (1981) J. Heterocycl. Chem. 18:599; Weijnen et al. (1992) J. Chem. Soc. Perkin Trans. 2:830) (19 mg, 0.052 mmol) in CH2Cl2 (4 mL) was added. The resulting solution was stirred for 24 h, and then ether (10 mL) was added to precipitate the salt byproduct, which was removed by filtration through celite. The removal of solvent under reduced pressure yielded compound 1 (37.5 mg, 0.047 mmol, 91% yield) in sufficient purity for experimental use.

Reference： [1]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - US2005/10059, 2005, A1 Location in patent: Page/Page column 6

12
[ 70069-04-4 ]
[ 570414-33-4 ]
[ 1312076-95-1 ]

Yield	Reaction Conditions	Operation in experiment
41%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; benzene at 70℃; Inert atmosphere;
	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; benzene at 70℃;

Reference： [1]Lu, Hsin-Hung; Ma, Yun-Sheng; Yang, Neng-Jye; Lin, Guan-Hong; Wu, Yun-Chung; Chen, Show-An [Journal of the American Chemical Society, 2011, vol. 133, # 25, p. 9634 - 9637]
[2]Liao, Sih-Hao; Li, Yi-Lun; Jen, Tzu-Hao; Cheng, Yu-Shan; Chen, Show-An [Journal of the American Chemical Society, 2012, vol. 134, # 35, p. 14271 - 14274]

13
[ 70069-04-4 ]
[ 58479-61-1 ]
[ 1550166-78-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 2-hydroxymethyl-18-crown-6 With 1H-imidazole In dichloromethane for 0.166667h; Inert atmosphere; Cooling; Stage #2: tert-butylchlorodiphenylsilane In dichloromethane at 20℃; Inert atmosphere;	4.1 General procedure for silylation of alcohols General procedure: In an oven-dried vial under argon atmosphere, alcohol (1.0mmol) was dissolved in dichloromethane (5mL) to which was added imidazole (2.0mmol). This solution was then stirred in an ice-bath for 10min. Silyl chloride (2.0mmol) was then added and the reaction was allowed to warm to room temperature. After completion, volatiles were removed under reduced pressure and the crude mixture was purified with silica gel chromatography using hexanes/EtOAc as eluent.

Reference： [1]Al-Huniti, Mohammed H.; Lu, Shuiyu; Pike, Victor W.; Lepore, Salvatore D. [Journal of Fluorine Chemistry, 2014, vol. 158, p. 48 - 52]

14
[ 70069-04-4 ]
[ 136449-55-3 ]
[ 1550166-89-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 2-hydroxymethyl-18-crown-6 With 1H-imidazole In dichloromethane for 0.166667h; Inert atmosphere; Cooling; Stage #2: biphenyldiisopropylsilyl chloride In dichloromethane at 20℃; Inert atmosphere;	4.1 General procedure for silylation of alcohols General procedure: In an oven-dried vial under argon atmosphere, alcohol (1.0mmol) was dissolved in dichloromethane (5mL) to which was added imidazole (2.0mmol). This solution was then stirred in an ice-bath for 10min. Silyl chloride (2.0mmol) was then added and the reaction was allowed to warm to room temperature. After completion, volatiles were removed under reduced pressure and the crude mixture was purified with silica gel chromatography using hexanes/EtOAc as eluent.

Reference： [1]Al-Huniti, Mohammed H.; Lu, Shuiyu; Pike, Victor W.; Lepore, Salvatore D. [Journal of Fluorine Chemistry, 2014, vol. 158, p. 48 - 52]

15
[ 108-24-7 ]
[ 70069-04-4 ]
[ 77887-92-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine In dichloromethane at 20℃; for 24h; Inert atmosphere;	I.3.1.(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methylacetate 1a InareactionvesselunderastreamofArgonwasdissolved0.45mmolofcrown-2-yl-methanolin5mLofanhydrousCH2Cl2.Then,3mmolofeach,aceticanhydrideandpyridinewereadded.Thereactionmixturewasstirredfor24hatroomtemperature.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield98%.1HNMR(400MHz,CDCl3)δ:4.15(dd,J=11.5and4.4Hz,1H),4.04(dd,J=11.5and5.6Hz,1H),3.73(m,3H),3.60(m,20H),2.00(s,3H);13CNMR(100MHz,CDCl3):δ170.7(s),71.3(d),70.9-70.6(10C),69.7(t)63.7(t),20.8(q);IR(NaCldisc):2875,1742,1587,1120cm-1;HRMSIEm/zcalculatedforC15H28O8[M]+336.1784,found:336.1791.

Reference： [1]Febles, Martín; Montalvão, Sofía; Crespín, Guillermo Díaz; Norte, Manuel; Padrón, José M.; Tammela, Päivi; Fernández, José J.; Daranas, Antonio Hernández [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5591 - 5593]

16
[ 1577-18-0 ]
[ 70069-04-4 ]
(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl (E)-hex-3-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; silica gel; dicyclohexyl-carbodiimide; at 20℃; for 24h;Inert atmosphere;	General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5591 - 5593

17
[ 2270-20-4 ]
[ 70069-04-4 ]
(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 5-phenylpentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Inert atmosphere;	Method1.“Steglichesterification”: General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

18
[ 5581-75-9 ]
[ 70069-04-4 ]
(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 6-phenylhexanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Inert atmosphere;	Method1.“Steglichesterification”: General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

19
[ 7170-40-3 ]
[ 70069-04-4 ]
(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 5-phenoxypentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Inert atmosphere;	Method1.“Steglichesterification”: General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

20
[ 7170-44-7 ]
[ 70069-04-4 ]
[ 2033052-63-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Inert atmosphere;	Method1.“Steglichesterification”: General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

21
[ 70069-04-4 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Inert atmosphere;	Method1.“Steglichesterification”: General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

22
[ CAS Unavailable ]
[ 70069-04-4 ]
[ 2033052-67-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Inert atmosphere;	Method1.“Steglichesterification”: General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

23
[ 1860-58-8 ]
[ 70069-04-4 ]
(1,4,7,10,13,16-hexaoxacyclooctadecan-2-yl)methyl 2-(3-(benzyloxy)phenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With dmap; silica gel; dicyclohexyl-carbodiimide at 20℃; for 24h; Inert atmosphere;	Method1.“Steglichesterification”: General procedure: InareactionvesselunderastreamofArgon,10mgofdrysilicagel,0.23mmolofacidand5mLofanhydrousCH2Cl2orTHFwereadded.Tothestirredmixture,0.45mmolofcrown-2-yl-methanoland4-DMAP(0.23mmol)andDCC(0.23mmol)wereadded.Thereactionmixturewasstirredfor24hatroomtemperatureandawhiteprecipitatewasappeared.Thesolidresiduewaseliminatedbyfiltration.Thesolutionwastransferredtoafunnelusing75mLofEt2Oandwashedwithsmallportionsof0.5Nhydrochloricacidanddistilledwater.Theorganicphasewasconcentratedinvacuoandchromatographed.TheprogressofthereactionwascheckedTLCbyconsumeofthestartingproducts(mobilephase:benzene:acetone:methanol:aceticacid6N.150:80:19:1).Overallyield60-95%.

24
[ 6293-66-9 ]
[ 70069-04-4 ]
[ 2464922-89-0 ]

Yield	Reaction Conditions	Operation in experiment
99.7%	With toluene-4-sulfonic acid at 280℃; for 4h; Microwave irradiation;	2.3; 11.3; 12.3; 19.3 3) Add 10 g of diphenyl p-toluenesulfonium iodonium salt, 22.2 g of intermediate B, and 0.4 g of p-toluenesulfonic acid to the reactor installed with the water separation device. Place the reactor in a microwave oven using 2500 MHz microwave for radiant heating The reaction temperature is controlled between 280°C. In this embodiment, the reflux water separation reaction is performed under radiant heating for 4 hours (that is, microwave irradiation time is 4 hours), and a large amount of white solids appear in the reaction system. The product was washed with ethanol and filtered twice, and after drying, a crown ether adsorbent II was obtained. The adsorbent yield was 99.7%.

Reference： [1]Current Patent Assignee: WANHUA CHEMICAL GROUP CO LTD - CN111253365, 2020, A Location in patent: Paragraph 0077; 0085-0087; 0147; 0152-0154; 0159-0160; 0208

25
[ 857419-46-6 ]
[ 70069-04-4 ]
[ 2445243-46-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 48h; Inert atmosphere;	1 Synthesis of the Monomers 9 and 10 A 100 mL three-necked flask, flamed and dried beforehand, has been loaded with chloromethyl-EDOT (0.5 g; 2.62 mmol; 1.0 eq.), hydroxy-methyl-18-crown-6 (0.526 g; 2.62 mmol; 1.0 eq.), potassium carbonate (0.725 g; 5.25 mmol; 2.0 eq.) and a catalytic amount of potassium iodide (0.043 g; 0.26 mmol; 0.1 eq.). The reactive medium has been solubilised in DMF (40 mL). This solution has been vigorously stirred at 100° C. for 24 hours under inert conditions. Then, a chloromethyl-EDOT equivalent has been added and the reaction has been carried on for 24 hours under the same conditions. The reactive mixture has been cooled down until returning to room temperature, and then it has been extracted with dichloromethane (3×20 mL). The combined organic fractions have been washed with water (20 mL) and dried with magnesium sulfate. The solvent has been evaporated under vacuum using a rotary evaporator and the product has been purified by alumina column chromatography as a stationary phase and with a dichloromethane/ethyl acetate/methanol solvent mixture (1:1:1). A caramel-coloured oil 10 (0.84 g; Rdt=72%) has been obtained in this manner. 1H-NMR (CDCl3, 400 MHz): δ(ppm): 6.33 (s, 2H); 4.23 (t, 2H); 4.11 (dd, 1H); 3.85 (m, 4H); 3.67 (m, 15H). 13C-NMR (CDCl3, 150 MHz): δ(ppm): 141.64, 141.34; 140.89; 100.34; 92.83; 77.23; 74.22; 73.06; 70.8; 65.96; 65.78; 65.49; 61.74; 41.54.

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF BORDEAUX 1; INSTITUT POLYTECHNIQUE DE BORDEAUX - US2022/56189, 2022, A1 Location in patent: Paragraph 0162-0163

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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 70069-04-4 ] {[proInfo.proName]}

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[ 70069-04-4 ] Synthesis Path-Downstream 1~25

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