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Chemical Structure| 66849-11-4 Chemical Structure| 66849-11-4

Structure of 66849-11-4

Chemical Structure| 66849-11-4

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Product Details of [ 66849-11-4 ]

CAS No. :66849-11-4
Formula : C10H11ClO2
M.W : 198.64
SMILES Code : O=C(Cl)C1=CC=CC=C1OC(C)C
MDL No. :MFCD11111058

Safety of [ 66849-11-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 66849-11-4 ]

* 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 [ 66849-11-4 ]

[ 66849-11-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 63746-12-3 ]
  • [ 66849-11-4 ]
  • [ 63746-15-6 ]
  • 2
  • [ 6645-46-1 ]
  • [ 66849-11-4 ]
  • C17H25NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.6 g With trifluoroacetic acid; at 0 - 45℃; for 1.33333h;Inert atmosphere; 5.0 g L -<strong>[6645-46-1]carnitine hydrochloride</strong> was dissolved in 28.0 g trifluoroacetic acid at 40-45 C. 11 g 2-isopropoxybenzoyl chloride was added dropwise to this solution at 0-20 C. over a period of 20 minutes. During the dropwise addition and the subsequent secondary reaction at 0-20 C., a nitrogen stream was led through the solution in order to expel the released hydrogen chloride gas. The reaction was tracked by DC (silica gel; eluent: chloroform:methanol:water:5% ammonia solution (55:39:1:5)). After approximately 1 hour, the reaction solution was quenched by adding 100 mL tent-butyl methyl ether. The precipitated product was taken up in 10 mL water, filtered over a column containing a weakly basic ion exchange resin, and concentrated under vacuum. The obtained solid was recrystallized from acetonitrile/acetone. Yield: 5.6 g [alpha]D20=-14.2 (c=1, water) Melting point: 142-144 C. RF: 0.28 (silica gel; eluent: chloroform:methanol:water:5% NH3 solution (55:39:1:5)) 1H-NMR (DMSO-d6, 300 MHz) delta: 7.61-6.95 (m, 4H) 5.69-5.57 (m, 1H) 4.76-4.62 (m, 1H) 3.89-3.68 (m, 2H) 3.14 (s, 9H) 2.43-2.09 (m, 2H) 1.27 (d, 6H) MS: 323 (M+1)
  • 3
  • [ 6645-46-1 ]
  • [ 66849-11-4 ]
  • (R)-(-)-3-(2-(hydroxybenzoyloxy)-4-trimethylammonio)butyric acid hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% 9.9 g <strong>[6645-46-1]L-<strong>[6645-46-1]carnitine hydrochloride</strong></strong> was dissolved in 50.0 g dichloroacetic acid at 60-65 C. 20.9 g 2-isopropoxybenzoyl chloride was added dropwise to this solution at -10 to 0 C. over a period of 60 minutes. During the dropwise addition and the subsequent secondary reaction at -10 to 0 C., the released hydrogen chloride gas was expelled from the reaction mixture by application of a slight vacuum (100-200 mbar). The reaction was tracked by DC (silica gel; eluent:chloroform:methanol:water:5% ammonia solution (55:39:1:5)). After approximately 1 hour, 9.4 g gaseous hydrochloric acid was introduced into the reaction solution. The reaction solution was heated at 45-50 C. for 30 minutes, a small quantity of water was added, and the reaction solution was further stirred at 20 to 25 C. The reaction was once again tracked by DC (silica gel; eluent: chloroform:methanol:water:5% ammonia solution (55:39:1:5)). The reaction mixture was then diluted with 200 mL ethyl acetate and inoculated with salicyloyl-L-carnitine HCl. As soon as the product began to crystallize, an additional 200 mL of ethyl acetate was added. The resulting suspension was cooled to 10 to 15 C., and stirring was performed for another hour at this temperature. The product that crystallized out was filtered off with suction, washed with 100 mL ethyl acetate, and dried overnight in a vacuum drying oven at 40-45 C. (0055) Yield: 14.6 g (92%) (0056) Melting point: 184-185 C. (0057) RF: 0.19 (silica gel; eluent: chloroform:methanol:water:5% NH3 solution (55:39:1:5)) [alpha]D20=-25.6 (c=1, water)
 

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