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[ CAS No. 34114-37-9 ] {[proInfo.proName]}

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Chemical Structure| 34114-37-9
Chemical Structure| 34114-37-9
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CAS No. :34114-37-9 MDL No. :
Formula : C9H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 168.19 Pubchem ID :-
Synonyms :

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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.

  • Downstream synthetic route of [ 34114-37-9 ]

[ 34114-37-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 34114-37-9 ]
  • [ 3245-45-2 ]
Reference： [1]Journal of medicinal chemistry,1963,vol. 6,p. 63 - 69
  • 2
  • [ 2088-24-6 ]
  • [ 150-76-5 ]
  • [ 34114-37-9 ]
YieldReaction ConditionsOperation in experiment
25.7 g (76%) In diethyl ether 4 2-(3-Methoxyphenoxy)ethanol PREPARATION 4 2-(3-Methoxyphenoxy)ethanol This compound was prepared by the procedure of Preparation 2. Thus, 36.5 g (0.2 mole) of 3-methoxyphenoxyacetic acid (Lancaster Synthesis, Inc., Windham, N.H. 03087) and 7.7 g (0.2 mole) of lithium aluminum hydride (Aldrich) in 600 ml of ethyl ether gave 25.7 g (76%) of light-yellow oil. Analysis: Calculated for C9 H12 O3: C, 64.27; H, 7.19. Found: C, 63.93; N, 7.10.
Reference： [1]Current Patent Assignee: PFIZER INC - US5192785, 1993, A
  • 3
  • [ 2088-24-6 ]
  • [ 90-05-1 ]
  • [ 34114-37-9 ]
YieldReaction ConditionsOperation in experiment
25.7 g (76%) In diethyl ether 4 Preparation 4 Preparation 4 2-(3-Methoxyphenoxy)ethanol. This compound was prepared by the procedure of Preparation 2. Thus, 36.5 g (0.2 mole) of 3-methoxyphenoxyacetic acid (Lancaster Synthesis, Inc., Windham, NH 03087) and 7.7 g (0.2 mole) of lithium aluminum hydride (Aldrich) in 600 ml of ethyl ether gave 25.7 g (76%) of light-yellow oil. Analysis: Calculated for C9 H12 O3: C, 64.27; H, 7.19; Found: C, 63.93; N, 7.10.
Reference： [1]Current Patent Assignee: PFIZER INC - US5194446, 1993, A
  • 4
  • [ 2088-24-6 ]
  • [ 34114-37-9 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 3-methoxyphenoxyacetic acid With borane In tetrahydrofuran at 20 - 30℃; Stage #2: With methanol In tetrahydrofuran at 35℃; R General Procedure R: Reduction of carboxylic acidA solution of carboxylic acid in an organic solvent (such as tetrahydrofuran or dioxane) (preferably THF) is added dropwise to a stirred solution of borane in THF at 0-500C, preferably about 23°C under an inert atmosphere. The reaction is stirred at warmed to 20-500C, preferably room temperature for 1-24 hours. The reaction is then quenched by cautious addition of methanol at 0-500C, preferably about room temperature. The crude product is concentrated under reduced pressure, taken up in ethyl acetate, washed with water, dried (Na2SO4), filtered, and concentratedExemplification of General Procedure R:Preparation of 2-(3-Methoxy-phenoxy)-ethanolBorane A 250ml three-necked round-bottomed flask equipped with temperature probe and nitrogen bubbler was charged with IM Borane/THF solution (60.4 ml, 60.4 m mol) and a solution of (3- Methoxy-phenoxy)-acetic acid (5.00 g, 27.4 mmol) in THF (2.0 ml) was added dropwise, maintaining reaction temperature below 3O0C. The reaction was allowed to stir at room temperature overnight. The reaction was quenched by dropwise addition of methanol (20 ml) maintaining the reaction temperature below 35°C. The reaction was stirred at room temperature for 4 hours and concentrated under reduced pressure to yield 2-(3-Methoxy-phenoxy)-ethanol (4.51 g, 98%) as a clear oil which was used without further purification. LCMS (Table 1, Method a) 2.43 min., m/z: 169 (M+H)+; 1H NMR (400 MHz, DMSO-J6) δ. 7.15 (m, IH), 6.48 (m, 3H), 4.81 (t, IH), 3.94 (t, 2H), 3.71 (s, 3H), 3.68 (m, 2H)
Reference： [1]Current Patent Assignee: ABBVIE INC - WO2008/79382, 2008, A1 Location in patent: Page/Page column 72

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