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Chemical Structure| 6059-29-6 Chemical Structure| 6059-29-6

Structure of 6059-29-6

Chemical Structure| 6059-29-6

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Product Details of [ 6059-29-6 ]

CAS No. :6059-29-6
Formula : C13H13NO2
M.W : 215.25
SMILES Code : OCC1=NC=CC=C1OCC2=CC=CC=C2

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Application In Synthesis of [ 6059-29-6 ]

* 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 [ 6059-29-6 ]

[ 6059-29-6 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 100-39-0 ]
  • [ 14173-30-9 ]
  • [ 6059-29-6 ]
YieldReaction ConditionsOperation in experiment
58% With potassium hydroxide; In ethanol; The starting material was prepared as follows: To a suspension of <strong>[14173-30-9]3-hydroxy-2-hydroxymethylpyridine hydrochloride</strong> (7.0 g, 12.4 mmol) in ethanol (37.5 ml) was added a solution of KOH pellets (85% 1.6 g, 24.7 mmol) in ethanol (25 ml). The reaction was stirred for 5 minutes at ambient temperature and then benzyl bromide was added (2.11 g, 12.36 mmol). The reaction mixture was stirred at ambient temperature for 48 hours, filtered and evaporated. The residue was purified by chromatography (EtOAc, CH2 Cl2) to give 3-benzyloxy-2-hydroxymethylpyridine as a colourless solid (1.55 g, 58%) ›J. Med. Chem., 15, (1972) 615! m.p. 78.7-79.2 C. MS (CI+):216 [M+H]+
  • 3
  • hydrochloride monohydrate [ No CAS ]
  • [ 100-39-0 ]
  • [ 14173-30-9 ]
  • [ 6059-29-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; acetone; EXAMPLE 1A 3-Benzyloxy-2-(hydroxymethyl)pyridine Sodium hydroxide (31.5 grams, 0.78 mole) was dissolved in 100 ml water and 100 ml of acetone was added followed by 3-hydroxy-2(hydroxymethyl)pyridine hydrochloride (63.8 grams; 0.39 mole). 250 ml of acetone was added followed by benzyl bromide (74.1 grams; 51.5 ml; 0.43 mole). The mixture was refluxed for a period of 4.5 hours and the acetone evaporated in vacuo. The aqueous layer was extracted with CH2 Cl2 (three times 150 ml) and the extracts dried (anhydrous Na2 SO4) and concentrated to yield 88.1 grams of a brown liquid. The brown liquid (88.1 grams) was dissolved in ether and ether-HCl added to form the hydrochloride salt. The HCl salt was filtered and the filter cake dissolved in water. The aqueous solution was basified to afford a brown pasty precipate which on trituration with ether afforded 58.7 grams of material. Recrystallization from ethanol yielded 31.6 grams of a tan solid, m.p. 79-80 C.
 

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