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Chemical Structure| 99183-34-3 Chemical Structure| 99183-34-3

Structure of 99183-34-3

Chemical Structure| 99183-34-3

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Product Details of [ 99183-34-3 ]

CAS No. :99183-34-3
Formula : C9H16O3
M.W : 172.22
SMILES Code : CC(C(C)CCCCC(O)=O)=O
MDL No. :MFCD20639044
InChI Key :WFGUTPGXNJPFOF-UHFFFAOYSA-N
Pubchem ID :71756573

Safety of [ 99183-34-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H318-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 99183-34-3 ]

* 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 [ 99183-34-3 ]

[ 99183-34-3 ] Synthesis Path-Downstream   1~7

  • 1
  • (+-)-2-acetyl-2-methyl-cyclohexane [ No CAS ]
  • [ 99183-34-3 ]
  • [ 583-60-8 ]
  • 2
  • [ 99183-34-3 ]
  • [ 637-60-5 ]
  • [ 1072069-90-9 ]
YieldReaction ConditionsOperation in experiment
83.7% With potassium acetate; In acetic acid; for 6.0h;Reflux; Example 10. Preparation of 3-(4-carboxybutyl)-2,3,5-trimethylindolenyne (compound 10) A mixture of 4-tolylhydrazine hydrochloride (compound 9) (825 mg; 5.2 mmole), glacial acetic acid (8 mL), 6-methyl-7-oxooctane acid (compound 5) (913 mg; 5.3 mmole), and anhydrous potassium acetate (980 mg; 10 mmole) was refluxed under stirring for 6 h. The solvent was removed, and the residue was dissolved in chloroform. The chloroform solution was washed with water, saturated solution of sodium chloride, and then dried over MgSO4. The solvent was removed and the residue was subjected to recrystallization from a mixture of diethyl ether - hexane, 1:10. 3-(4-Carboxybutyl)-2,3,5-trimethylindolenyne (compound 10) was obtained as a dark orange powder with yield of 1.13 g (83.7%). λmax 254 nm. Mass-spectrum (MALDI) (C16H21NO2): found m/z 260.7, calculated m/z 259.34. 1H-NMR (CDCl3), δ (ppm): 0.6-0.83 (2H, m, CH2CH2CH2CH2COOH); 1.25 (3H, s, 3-CH3); 1.46 (2H, m, CH2CH2CH2CH2COOH); 1.72-1.88 (2H, m, CH2CH2CH2CH2COOH); 2.09-2.18 (2H, m, CH2CH2CH2CH2COOH); 2.28 (3H, s, 2-CH3); 2.37 (3H, s, 5-CH3), 7,01-7.4 (3H, m, ArH), 10.11 (1H, s, COOH)
  • 3
  • [ 99183-34-3 ]
  • [ 54005-64-0 ]
  • C15H18NO5S(1-) [ No CAS ]
  • 4
  • [ 99183-34-3 ]
  • [ 100-63-0 ]
  • 5-(2,3-dimethyl-3H-indol-3-yl)pentanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In acetic acid; at 118.0℃; for 3.5h; Example 6. Preparation of 2,3-dimethyl-3-(4-carboxybutyl)indolenyne (compound 6) A glass vial was charged with 6-methyl-7-oxooctane acid (compound 5) (723.3 mg; 4.2 mmole), phenyl hydrazines (454.2 mg; 413.7 μL; 4.2 mmole), and glacial acetic acid (4.2 mL). The mixture was heated at 118C for 3.5 h. The solvent was removed and the oily residue was dissolved in chloroform. The chloroform solution was washed with water, saturated solution of sodium chloride, and dried over MgSO4. The solvent was removed and the residue subjected to recrystallization from ethyl acetate-hexane (0.6:2) mixture. 2,3-Dimethyl-3-(4-carboxybutyl)-indolenyne (compound 6) was obtained as a yellow-orange powder, yield was 0.8 g (78%). λmax 256 nm. Mass-spectrum (MALDI) (C15H19NO2): found m/z 246.3, calculated m/z 245.32. 1H- NMR (CDCl3), δ (ppm): 0.56-0.81 (2H, m, CH2CH2CH2CH2COOH); 1.28 (3H, s, 3-CH3); 1.43-1.51 (2H, m, CH2CH2CH2CHCOOH); 1.76-1.92 (2H, m, CH2CH2CH2CH2COOH); 2.13-2.21 (2H, m, CH2CH2CH2CH2COOH); 2.24 (3H, s, 2-CH3); 7.18-7.54 (4H, m, ArH)
  • 5
  • [ 99183-34-3 ]
  • [ 98-71-5 ]
  • [ 1072069-89-6 ]
YieldReaction ConditionsOperation in experiment
83% Example 8. Preparation of 2,3-dimethyl-3-(4-carboxybutyl)-5-sulfoindolenyne, potassium salt (compound 8) A mixture of phenylhydrazine-p-sulphonic acid (compound 7) (1.8 g; 9.7 mmole), 6-methyl-7-oxooctane acid (compound 5) (2.0 g; 11.6 mmole), and glacial acetic acid (15 mL) was refluxed under stirring for 8 h, then an additional amount of acetic acid was added and treated with activated carbon. The solvent was removed and the residue was dissolved in methanol (10 mL). To solution obtained, there are added dropwise the solution of potassium hydroxide (600 mg; 10,56 mmole) in methanol (7 mL), isopropyl alcohol (15 mL), and diethyl ether (2 mL). The precipitate formed was collected by filtration and dried in vacuum desiccator over P2O5. 2,3-Dimethyl-3-(4-carboxybutyl)-5-sulfoindolenyne, potassium salt (compound 8) was obtained with yield of 3.47 g (83%), λmax 258 nm. Mass-spectrum (MALDI) (C15H19NO5S): found m/z 327.2, calculated m/z 325.38. 1H-NMR (D2O), δ (ppm): 0.45-0.7 (2H, m, CH2CH2CH2CH2COOH); 1.31 (3H, s, 3-CH3); 1.36 (2H, m, CH2CH2CH2CH2COOH); 1.88-2.14 (4H, m, CH2CH2CH2CH2COOH); 7.53 (1H, d, ArH), 7.8 (2H, m, ArH)
  • 6
  • [ 5601-58-1 ]
  • [ 99183-34-3 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride; water; for 6.0h;Reflux; Example 5. Preparation of 6-methyl-7-oxooctane acid (compound 5) A mixture of diluted (2:1) hydrochloric acid (37 mL) and 6-methyl-7-oxooctane acid, methyl ester (compound 4) (9.11 g; 0.049 mole) was refluxed under stirring for 6 h. The reaction produced two immiscible layers. The reaction mixture was extracted with ether. Ethereal extracts were combined. The solvent was removed and the residue was fractionated under vacuum. Fraction having Bp= 100-143C/0.1-0.01 mm Hg was drawn to obtain 6-methyl-7-oxooctane acid (compound 5) yield of 5.9 g (75%). 1H-NMR (CDCl3), δ (ppm): 1.06 (3H, d, 6-CH3); 1.25-1.39 (3H, m, 5-CH2, 4-CH2); 1.58-1.69 (3H, m, 3-CH2, 4-CH2); 2.12 (3H, s, 8-CH3); 2.33 (2H, t, J=7.5, 2-CH2); 2.5 (1H, m, 6-CH).
  • 7
  • [ 58648-13-8 ]
  • [ 99183-34-3 ]
  • [ 583-60-8 ]
 

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