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[ CAS No. 5337-04-2 ]

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2D
Chemical Structure| 5337-04-2
Chemical Structure| 5337-04-2
Structure of 5337-04-2 *Storage: {[proInfo.prStorage]}

Quality Control of [ 5337-04-2 ]

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Related Doc. of [ 5337-04-2 ]

SDS

Product Details of [ 5337-04-2 ]

CAS No. :5337-04-2MDL No. :MFCD10480216
Formula : C7H10O5 Boiling Point : 412.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :174.15Pubchem ID :219303
Synonyms :

Computed Properties of [ 5337-04-2 ]

TPSA : 83.8 H-Bond Acceptor Count : 5
XLogP3 : -0.3 H-Bond Donor Count : 2
SP3 : 0.71 Rotatable Bond Count : 2

Safety of [ 5337-04-2 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5337-04-2 ]

  • Upstream synthesis route of [ 5337-04-2 ]
  • Downstream synthetic route of [ 5337-04-2 ]

[ 5337-04-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5382-77-4 ]
  • [ 5337-04-2 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With sodium hydroxide In water at 20℃; for 28.00 h;
Stage #2: With hydrogenchloride In water
Diethyl tetrahydro-2H-pyran-4,4-dicarboxylate (4.04 g, 20 mmol) is suspended in a 30 percent aqueous sodium hydroxide solution (10 mL), and the mixture is stirred at room temperature for 28 hours. The pH value of the reaction solution is adjusted to pH 1 with conc. hydrochloric acid, and the mixture is separated into water and ethyl acetate. The organic layer is dried over anhydrous sodium sulfate, and the solvent is evaporated. Ethyl acetate (30mL) is added to the obtained crude product, and the mixture is washed by repulping, and the resulting solid is collected by filtration, and dried to give tetrahydro-4H-pyran-4,4-dicarboxylic acid (3.19 g, 18.3 mmol, 92 percent). 1H-NMR (DMSO-d6) δ: 1.90 (4H, t, J=5.3Hz), 3.55 (4H, t, J=5.3Hz), 12.93 (2H, s).
90.2% With potassium hydroxide In ethanol; water Oxane-4,4-dicarboxylic Acid
To a stirred solution of diethyl oxane-4,4-dicarboxylate (40.0 g., 173 mmol) in ethanol (100 mL) was added a solution of potassium hydroxide (21.4 g, 382 mmol) in ethanol (300 mL).
After the completion of the addition, the reaction mixture was stirred for 15 min at ambient temperature and then refluxed for 2.5 h.
Water (40 mL) was added to the thick, white suspension, and then the solvent was removed by rotary evaporation.
Water (40 mL) was added to the remaining residue and the resulting mixture then acidified with concentrated sulfuric acid (20 mL).
The acidic solution was extracted with diethyl ether (3*300 mL) and the combined organic layers were dried (Na2SO4).
Removal of solvent by rotary evaporation yielded the product (27.3 g, 90.2percent yield).
61%
Stage #1: Cooling with ice; Reflux
Stage #2: With hydrogenchloride In water
Reference Example 3; Tetrahydro-pyran-4,4-dicarboxylic acid; 6M potassium hydroxide solution (10 mL, 60 mmol) was added to an ice-cooled solution of tetrahydropyran-4,4-dicarboxylic acid diethyl ester (5 g, 21.7 mmol) in ethanol (40 mL) and heated at reflux overnight. The volatiles were evaporated, the residue diluted with water and acidified with conc. hydrochloric acid. The mixture was allowed to stand overnight then extracted with ether (3.x.25 mL). The combined ether layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford tetrahydro-pyran-4,4-dicarboxylic acid (2.3 g, 61percent) as a white solid.
61%
Stage #1: With potassium hydroxide; water In ethanolHeating / reflux
Stage #2: With hydrogenchloride In water
Reference Example 4: Tetrahydro-pyran-4,4-dicarboxylic acid. 6M potassium hydroxide solution (10 mL, 60 mmol) was added to an ice-cooled solution of tetrahydropyran-4,4-dicarboxylic acid diethyl ester (5 g, 21.7 mmol) in ethanol (40 mL) and heated at reflux for overnight. The volatiles were evaporated, the residue diluted with water and acidified with cone, hydrochloric acid. The mixture was allowed to stand overnight then extracted with ether (3 x 25 mL). The combined ether layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford tetrahydro-pyran-4,4-dicarboxylic acid (2.3 g, 61percent) as a white solid.

Reference: [1] Patent: EP1514869, 2005, A1. Location in patent: Page/Page column 52
[2] Patent: US2004/220214, 2004, A1
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 47, # 1 + 2, p. 157 - 164
[4] Helvetica Chimica Acta, 1997, vol. 80, # 5, p. 1528 - 1551
[5] Patent: US2011/9390, 2011, A1. Location in patent: Page/Page column 14
[6] Patent: WO2008/62182, 2008, A1. Location in patent: Page/Page column 110-111
[7] Collection of Czechoslovak Chemical Communications, 1932, vol. 4, p. 259,263
  • 2
  • [ 111511-90-1 ]
  • [ 5337-04-2 ]
Reference: [1] Patent: US4870070, 1989, A
  • 3
  • [ 111-44-4 ]
  • [ 108-59-8 ]
  • [ 5337-04-2 ]
Reference: [1] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 16
  • 4
  • [ 30431-99-3 ]
  • [ 5337-04-2 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 2525,2529
  • 5
  • [ 34270-90-1 ]
  • [ 105-53-3 ]
  • [ 5337-04-2 ]
Reference: [1] Chemische Berichte, 1917, vol. 50, p. 1658
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