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Chemical Structure| 1000016-95-4 Chemical Structure| 1000016-95-4

Structure of 1000016-95-4

Chemical Structure| 1000016-95-4

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Product Details of [ 1000016-95-4 ]

CAS No. :1000016-95-4
Formula : C12H12O3
M.W : 204.22
SMILES Code : O=C(O)C1=CC=CC(C2=CCOCC2)=C1
MDL No. :MFCD24498395

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Application In Synthesis of [ 1000016-95-4 ]

* 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 [ 1000016-95-4 ]

[ 1000016-95-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1000016-95-4 ]
  • [ 1000016-93-2 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20.0℃; for 72.0h; To a stirred solution of 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (10.7g) (prepared according to WO9709328) and tetrakis(triphenylphosphine)palladium (1.78g) in toluene (594ml) was added 3-cynophenylboronic acid (7.42g), dissolved a minimum amount of ethanol, followed by a 2M aqueous sodium carbonate solution (50.5ml). The resulting mixture was heated at reflux for 16 hours. After filtration, the mixture was concentrated to dryness in vacuo and the residue partitioned between dichloromethane and brine. The organics were dried over magnesium sulphate, filtered and concentrated to dryness. The residue was then purified by SiO2 chromotograhy, eluting with a zso-hexane to 15% ethyl acetate in iso-hexane gradient to yield 3-(3,6-dihydro-2H-pyran-4- yl)benzonitrile (5.9Ig). A solution of 3-(3,6-dihydro-2H-pyran-4-yl)benzonitrile (1.64g) in n-butanol (5ml) and 5M aqueous sodium hydroxide solution (5ml) was heated at reflux for 16 hours. The cooled reaction mixture was concentrated to dryness in vacuo and the residue taken up into water and acidified using a 2M aqueous hydrochloric acid solution. The mixture was then extracted into ethyl acetate (2x100ml) and the combined organics dried over magnesium sulphate, filtered and concentrated to dryness to give 3-(3,6- dihydro-2H-pyran-4-yl)benzoic acid (1.6Og). To a solution of 3-(3,6-dihydro-2H-pyran-4- yl)benzoic acid (6.3Ig) in ethanol (200ml) was added 10% palladium on carbon (0.4Og) and the mixture stirred under a balloon of hydrogen at room temperature for 72 hours. The reaction mixture was fltered through diatomaceous earth (Celite) and the filtrate concentrated to dryness in vacuo to afford 3-(tetrahydro-2H-rhoyran-4-yl)benzoic acid (6.12g). NMR Spectrum: (DMSO-d6) 12.90 (s, 1eta), 7.83 - 7.76 (m, 2eta), 7.53 (d, J = 7.3 Hz, IH), 7.44 (t, J = 7.6 Hz, IH)3 3.99 - 3.91 (m, 2H), 3.44 (td, J = 11.2, 3.1 Hz, 2H), 2.91 - 2.79 (m, IH), 1.77 - 1.59 (m, 4H)
 

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