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2-(7-Methoxynaphthalen-1-yl)ethan-1-ol
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[ CAS No. 99416-99-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 99416-99-6
Chemical Structure| 99416-99-6
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CAS No. :99416-99-6 MDL No. :
Formula : C13H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 202.25 Pubchem ID :-
Synonyms :

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Precautionary Statements: UN#:
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Application In Synthesis of [ 99416-99-6 ]

* 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 [ 99416-99-6 ]

[ 99416-99-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 6836-21-1 ]
  • [ 99416-99-6 ]
YieldReaction ConditionsOperation in experiment
97% With sodium tetrahydroborate; ethanol; calcium chloride; In tetrahydrofuran; at 5 - 20℃; 150 ml of ethanol is loaded into a three-necked reaction flask, magnetically stirred and equipped with a temperature probe, and cooled to 5C. When the temperature of 5C has been reached, 11.3 g of powdered calcium chloride(0.102 mol) is added, followed by 8.2 g of sodium borohydride (0.217 moles). After a few minute stirring at 5C, 10 g of <strong>[6836-21-1]2-(7-methoxynaphthalen-1-yl)acetic acid ethyl ester</strong> 4 (41 mmols), dissolved in 100 ml of anhydrous THF, is added, the temperature being maintained under 10C. At the end of the addition the temperature is increased to room temperature and maintained at that temperature for about 2 hours. 5 ml of water is added slowly at the end of the reaction. 40 ml oftoluene and 20 ml of 30% HCl are then added. The phases are separated by re-extracting the aqueous phase with 20ml of toluene. The combined organic phases are washed with 40 ml of water, and then concentrated under vacuum to dryness to obtain 8.0 g of 2-(7-methoxynaphthalen-1-yl)ethanol 12. Yield 97%. The intermediate obtained was identifiedby NMR analysis: 1H NMR (400 MHz, DMSO-d6) delta 7.83 (d, 2H), 7.70 (m, 1H), 7.36 (m, 2H), 7.27 (m, 1H), 7.18 (m, 1H),3.92 (s, 3H), 3.75 (t, 2H), 3.29 (s, 1H), 3.19 (m, 1H).
Reference： [1]Patent: EP2703383,2014,A1 .Location in patent: Paragraph 0037
[2]Journal of Organic Chemistry,1985,vol. 50,p. 5550 - 5556
  • 2
  • [ 6836-22-2 ]
  • [ 99416-99-6 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 30℃; To a solution of 7-methoxy- 1 -naphthyl acetic acid (Formula II, 60 g) in tetrahydrofuran (240 mL), a suspension of lithium aluminum hydride (16.8 g) in tetrahydrofuran (1500 mL) was slowly added over a period of 15 to 20 minutes at 0C. The reaction mixture was stirred for 4 hours at 25C to 30C. After completion of the reaction, ethyl acetate (120 mL) was added, followed by the slow addition of 5N hydrochloric acid (100 mL) over a period of 30 minutes at 0C. The reaction mixture was stirred and the layers were allowed to settle. The organic layer was separated and removed under vacuum (40C to 45C, -100 mbar). The residue so obtained was used for the next example.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 30℃; Example 1 : Preparation of (7-Methoxy- l-Naphthyl)Ethanol Formula III To a solution of 7-methoxy- 1 -naphthyl acetic acid (Formula II, 60 g) in tetrahydrofuran (240 mL), a suspension of lithium aluminum hydride (16.8 g) in tetrahydrofuran (1500 mL) was slowly added over a period of 15 minutes to 20 minutes at 0C. The reaction mixture was stirred for 4 hours at 25C to 30C. After completion of the reaction, ethyl acetate (120 mL) was added, followed by the slow addition of 5N hydrochloric acid (100 mL) over a period of 30 minutes at 0C. The reaction mixture was stirred and the layers were allowed to settle. The organic layer was separated and removed under vacuum (40C to 45C, -100 mbar). The residue so obtained was used for the next step. Example 2: Preparation of 2-(7-Methoxynaphthalen- 1 -Yl)Ethyl 4-Nitrobenzene Sulfonate
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 30℃; To a solution of 7-methoxy-1-naphthyl acetic acid (Formula II, 60 g) in tetrahydrofuran (240 mL), a suspension of lithium aluminum hydride (16.8 g) in tetrahydrofuran (1500 mL) was slowly added over a period of 15 to 20 minutes at 0 C. The reaction mixture was stirred for 4 hours at 25 C. to 30 C. After completion of the reaction, ethyl acetate (120 mL) was added, followed by the slow addition of 5N hydrochloric acid (100 mL) over a period of 30 minutes at 0 C. The reaction mixture was stirred and the layers were allowed to settle. The organic layer was separated and removed under vacuum (40 C. to 45 C., ?100 mbar). The residue so obtained was used for the next example.
Reference： [1]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 1875 - 1887
[2]Patent: WO2013/80095,2013,A1 .Location in patent: Page/Page column 8
[3]Patent: WO2013/54273,2013,A2 .Location in patent: Page/Page column 10; 11
[4]Tetrahedron Letters,2014,vol. 55,p. 3885 - 3887
[5]Patent: US2014/336380,2014,A1 .Location in patent: Paragraph 0042; 0043
  • 3
  • [ 99416-99-6 ]
  • [ 139525-77-2 ]
Reference： [1]Patent: EP2322508,2011,A1
[2]Patent: EP2322508,2011,A1
  • 4
  • [ 99416-99-6 ]
  • [ 138113-09-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 15 °C 2: dimethyl sulfoxide / 50 °C 3: sodium hydroxide; methanol / 18 h / 40 °C
Reference： [1]Current Patent Assignee: PROCOS SPA - EP2703383, 2014, A1

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