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Chemical Structure| 40624-07-5 Chemical Structure| 40624-07-5

Structure of 40624-07-5

Chemical Structure| 40624-07-5

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Product Details of [ 40624-07-5 ]

CAS No. :40624-07-5
Formula : C7H12Cl2O
M.W : 183.08
SMILES Code : C(C(CCCCl)=O)CCCl
MDL No. :MFCD00019001
Boiling Point : No data available
InChI Key :SCKUIKDAPAUGBE-UHFFFAOYSA-N
Pubchem ID :246749

Safety of [ 40624-07-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 40624-07-5 ]

* 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 [ 40624-07-5 ]

[ 40624-07-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 40624-07-5 ]
  • [ 10323-39-4 ]
  • C17H26Cl2O2 [ No CAS ]
  • 2
  • [ 40624-07-5 ]
  • [ 10323-39-4 ]
  • [ 1080022-06-5 ]
YieldReaction ConditionsOperation in experiment
83% <strong>[10323-39-4]4-Bromo-2-tert-butylphenol</strong> (1.00 g, 4.37 mmol) was dissolved in THF (50 mE) under a nitrogen atmosphere, tert-BuLi (1.7 M in pentane 5.86 g, 15.28 mmol) was added thereto at -78 C using a syringe. The reaction was allowed to proceed while stirring at -78 C for 2 hours. 1,7-Dichloro-heptane-4-one (0.96 g, 5.24 mmol) and LiCl (0.22 g, 5.24 mmol) were added to the reaction mixture while stirring -78 C. over 2 hours. After the solution was stirred for 2 hours at -78 C., aqueous saturated NH4Cl solution (15 mL) was added to quench the reaction. The product was extracted using diethyl ether (3×15 mL). After the combined organic phase was dried over anhydrous MgSO4, the solvent was removed with rotary evaporator to give an oily residue. The major side product of the reaction was 2-tert-butyl phenol, generated by the protonation of the lithiated compound. It was not easy to remove the side product from the hydrogenated product by column chromatography. Therefore, the side product was eliminated by the following procedure: the oily residue was transferred into a separatory funnel, and then diethyl ether (10 mL) and aqueous KOH solution (22 w %, 5 mL) were added. The mixture was vigorously shaken to give three phases. The upper layer was diethyl ether phase. The middle layer was a potassium phenolate of the desired products. The bottom layer was an aqueous phase containing potassium 2-tert-butylphenolate. After the bottom layer was discarded, aqueous saturated NH4Cl solution (5 mL) was added. By the addition, the phenolate anion of the desired products was protonated to be soluble in the diethyl ether phase. The ether phase was collected and dried over anhydrous MgSO4. The solvent was removed with a rotary evaporator to give an oily residue which was purified by column chromatography. The benzylic tertiary alcohol was obtained by eluting hexane and ethyl acetate (v/v, 2:1). The obtained compound was then dissolved in ethanol (5 mL). Pd on activated charcoal (10 w %) was added, and then the solution was stirred overnight at room temperature under an atmospheric pressure of H2 gas. The solution was filtered over Celite, and then solvent was removed with a rotary evaporator to give a residue, which was purified by column chromatography on silica gel eluting with hexane and ethyl acetate (v/v, 2:1) to obtain Compound 30 (yield: 83%). 1H NMR (CDCl3): delta 7.02 (d, J=2.0 Hz, 1H, m-H), 6.84 (dd, J=8.0, 2.0 Hz, 1H, m-H), 6.62 (d, J=8.0 Hz, 1H, o-H), 4.93 (s, 1H, OH), 3.49 (t, J=5.6 Hz, 4H, -CH2Cl), 2.49 (quintet, J=4.8 Hz, 1H, -CH-), 1.88-1.75 (m, 4H, CH2), 1.72-1.61 (m, 4H, CH2), 1.45 (s, 9H, -C(CH3)3) ppm. 13C {1H}NMR (CDCl3): delta 152.36, 135.86, 135.82, 126.02, 125.21, 115.38, 45.26, 44.34, 34.56, 34.14, 30.66, 29.71 ppm
 

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