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Chemical Structure| 18181-71-0
Chemical Structure| 18181-71-0
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Product Details of [ 18181-71-0 ]

CAS No. :18181-71-0 MDL No. :MFCD01095842
Formula : C9H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 168.19 Pubchem ID :-
Synonyms :

Safety of [ 18181-71-0 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18181-71-0 ]

* 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 [ 18181-71-0 ]

[ 18181-71-0 ] Synthesis Path-Downstream   1~24

  • 1
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YieldReaction ConditionsOperation in experiment
92% Stage #1: 2-methoxy-phenol With tetrabutylammomium bromide; sodium hydroxide In water at 30℃; for 0.25h; Stage #2: 2-chloro-ethanol In water at 20 - 70℃; Preparation of 2-(2-methoxyphenoxy)ethanol,12: To a solution of 10 (50.0 g, 0.402 mol) in water(200 mL) added TBAB (3.5 g, 0.01 mol) and sodiumhydroxide (48.3 g, 1.208 mol) then stirred together for15 min at 30°C. To this mixture, added 2-chloroethanol11 (38.9 g, 0.483 mol) at RT and stirred for 2 hr at70°C for completion of the reaction. The reactionmixture was cooled to RT and extracted the productwith toluene (200 mL). The organic layer wasconcentrated under reduced pressure to afford the titlecompound 12 (62.3 g, yield: 92.0%). IR (KBr): 3390(-OH), 2838 cm-1 (-OCH3); 1H NMR (400 MHz,DMSO-d6/TMS): 6.95 (m, 2H,-aromatic), 6.85 (m, 2H,-aromatic), 4.8 (s, 1H,-OH), 3.95 (m, 2H,-OCH2), 3.75(s, 3H,-OCH3), 3.7 (m, 2H,-CH2); MS: m/z (M)168.Anal. Calcd for C9H12O3 (168.19): C, 64.27; H, 7.19;O, 28.54. Found: C, 64.31; H, 7.17; O, 28.52 %.
With sodium hydroxide
With sodium hydroxide
With sodium hydroxide In water at 20℃; for 24h; Inert atmosphere; 2.1.1 Synthesis of compound 3 General procedure: A mixture of 4-bromophenol(0.116 mol) and 2-chloroethanol (1.16 mol) in 10% aqueous NaOH solution (400ml) was stirred under a nitrogen atmosphere at rt. After 24 h, the mixture wasextracted with CH2Cl2 (2 × 150 ml). The CH2Cl2extracts were combined, washed with 10% aqueous NaOH (2 × 150 ml) and water (3× 150 ml), dried over anhydrous MgSO4. After the solvent wasevaporated, the residue was recrystallized from hexane-ethanol to give 3 as white crystals (23.08 g, 92%) forthe next step.Yield 92%. White crystals, mp 52-53 oC.
With sodium hydroxide

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  • 9
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  • 20
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YieldReaction ConditionsOperation in experiment
1: 67 %Spectr. 2: 38 %Spectr. 3: 44 %Spectr. With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium carbonate; 6,6′‐dihydroxyl‐2,2′‐bipyridine In 1,4-dioxane; water at 130℃; for 1h; Sealed tube;
  • 21
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YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 2 h / 0 - 30 °C 2: N,N-dimethyl-formamide / 3 h / 170 °C
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YieldReaction ConditionsOperation in experiment
1: 5.4 %Chromat. 2: 13.7 %Chromat. 3: 6.9 %Chromat. 4: 5.1 %Chromat. 5: 27 %Chromat. 6: 11.2 %Chromat. 7: 8.1 %Spectr. 8: 37 %Chromat. With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In 1,3,5-trimethyl-benzene at 160℃; for 20h; Inert atmosphere; II. Experimental Procedures General procedure: Into a 3-mL glass tube, catalyst (4.5 μmol) and substrate (1 or c5; 90 μmol) were placed. After dinitrogen gaswas filled in the glass tube, 180 μL of mesitylene or xylene was added. In the open system reactions, the glasstube was connected to leak line. In the reactions conducted under 1 atm of dihydrogen, the glass tube wasconnected to a balloon filled with dihydrogen. The glass tube was placed on an aluminum heating block. Afterstirring at the indicated temperature and for the indicated time, a certain amount of dodecane (ca. 7.5 mg) wasadded as an internal standard and the products were analyzed by GC. After removal of all the volatiles, theproducts were also analyzed by 1H NMR in CDCl3 and the conversion of the substrate 1 and the yields of c1, c3and c4 were calculated with a certain amount of 1,1,2,2-tetrachloroethane (ca. 7.7 mg) as an internal standard.
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YieldReaction ConditionsOperation in experiment
1: 6.7 %Chromat. 2: 16.7 %Chromat. 3: 5.9 %Chromat. 4: 7.5 %Chromat. 5: 19.5 %Chromat. 6: 12.1 %Chromat. 7: 46 %Chromat. With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In 1,3,5-trimethyl-benzene at 140℃; for 20h; II. Experimental Procedures General procedure: Into a 3-mL glass tube, catalyst (4.5 μmol) and substrate (1 or c5; 90 μmol) were placed. After dinitrogen gaswas filled in the glass tube, 180 μL of mesitylene or xylene was added. In the open system reactions, the glasstube was connected to leak line. In the reactions conducted under 1 atm of dihydrogen, the glass tube wasconnected to a balloon filled with dihydrogen. The glass tube was placed on an aluminum heating block. Afterstirring at the indicated temperature and for the indicated time, a certain amount of dodecane (ca. 7.5 mg) wasadded as an internal standard and the products were analyzed by GC. After removal of all the volatiles, theproducts were also analyzed by 1H NMR in CDCl3 and the conversion of the substrate 1 and the yields of c1, c3and c4 were calculated with a certain amount of 1,1,2,2-tetrachloroethane (ca. 7.7 mg) as an internal standard.
  • 24
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YieldReaction ConditionsOperation in experiment
1: 14.3 %Chromat. 2: 6.1 %Chromat. 3: 7.2 %Chromat. 4: 25 %Chromat. 5: 20.8 %Chromat. 6: 27.7 %Chromat. With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In 1,3,5-trimethyl-benzene at 140℃; for 20h; Inert atmosphere; II. Experimental Procedures General procedure: Into a 3-mL glass tube, catalyst (4.5 μmol) and substrate (1 or c5; 90 μmol) were placed. After dinitrogen gaswas filled in the glass tube, 180 μL of mesitylene or xylene was added. In the open system reactions, the glasstube was connected to leak line. In the reactions conducted under 1 atm of dihydrogen, the glass tube wasconnected to a balloon filled with dihydrogen. The glass tube was placed on an aluminum heating block. Afterstirring at the indicated temperature and for the indicated time, a certain amount of dodecane (ca. 7.5 mg) wasadded as an internal standard and the products were analyzed by GC. After removal of all the volatiles, theproducts were also analyzed by 1H NMR in CDCl3 and the conversion of the substrate 1 and the yields of c1, c3and c4 were calculated with a certain amount of 1,1,2,2-tetrachloroethane (ca. 7.7 mg) as an internal standard.
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