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[ CAS No. 1459-95-6 ] {[proInfo.proName]}

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Chemical Structure| 1459-95-6
Chemical Structure| 1459-95-6
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Product Details of [ 1459-95-6 ]

CAS No. :1459-95-6 MDL No. :MFCD00167791
Formula : C14H20O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 252.31 Pubchem ID :-
Synonyms :

Safety of [ 1459-95-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 1459-95-6 ]

* 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 [ 1459-95-6 ]

[ 1459-95-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1459-95-6 ]
  • [ 17071-62-4 ]
YieldReaction ConditionsOperation in experiment
98% With lithium aluminium tetrahydride In tetrahydrofuran for 8h; Reflux;
92% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 65℃; for 3h;
86.7% With lithium aluminium tetrahydride In tetrahydrofuran for 70h; Heating;
With tetrahydrofuran; sodium aluminum tetrahydride
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 65℃; for 4h; Inert atmosphere;

  • 2
  • [ 186581-53-3 ]
  • [ 39269-10-8 ]
  • [ 1459-95-6 ]
  • 4
  • [ 67-56-1 ]
  • [ 39269-10-8 ]
  • [ 1459-95-6 ]
YieldReaction ConditionsOperation in experiment
sulfuric acid; In water; 1,2-dichloro-ethane; at 62℃; for 10h;Product distribution / selectivity; The synthesis of 2-methacryloyloxy-2-(3-(2-hydroxy-2-propyl)1-1-adamantyl)propane was performed by the following method. First, according to the method described in Japanese Patent Application Laid-open No. 2002-167342, 1000 g of 1,3-dihydroxyadamantane was synthesized from adamantane. Next, a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a Dimroth condenser was charged with 100 g of 1,3-dihydroxyadamantane, 500 mL of 1,2-dichloroethane and 800 g of 96percent sulfuric acid, and further 300 g of formic acid was dropped into the flask for 1 h. Thereafter, the contents of the flask were reacted at 25° C. for 10 h. The resultant reaction solution was filtered to separate precipitated crystals therefrom. The thus separated crystals were washed with water to obtain 140 g of <strong>[39269-10-8]1,3-adamantanedicarboxylic acid</strong>. Then, a four-necked flask equipped with a stirrer, a thermometer and a Dimroth condenser was charged with 140 g of <strong>[39269-10-8]1,3-adamantanedicarboxylic acid</strong>, 12 g of 96percent sulfuric acid, 200 g of methanol and 1000 mL of 1,2-dichloroethane, and the contents of the flask were reacted at 62° C. for 10 h.After completion of the reaction, the resultant reaction solution was separated into an organic phase and a water phase. The organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution, and then concentrated. The thus obtained crystals were separated from the organic phase by filtration, thereby obtaining 150 g of methyl 1,3-adamantanedicarboxylate. Next, a four-necked flask equipped with a stirrer, a thermometer, a Dimroth condenser and a dropping funnel was charged with 100 g of methyl 1,3-adamantanedicarboxylate and 500 mL of tetrahydrofuran, and then 600 mL of a 3M magnesium methyl bromide/diethyl ether solution was dropped into the flask for 1 h. Thereafter, the contents of the flask were stirred at 25° C. for 3 h, and then mixed with water to terminate the reaction. The resultant reaction solution was separated into an organic phase and a water phase. The thus separated organic phase was concentrated to obtain 90 g of 1,3-adamantanediisopropanol.Next, a five-necked flask equipped with a stirrer, a thermometer, a Dimroth condenser and two dropping funnels was charged with 90 g of 1,3-adamantanediisopropanol and 100 mL of 1,2-dichloroethane, and then 63 g of methacryloyl chloride and 81 g of triethylamine were simultaneously dropped into the flask for 1 h. Thereafter, the contents of the flask were stirred at 25° C. for 3 h, and then mixed with water to terminate the reaction. The resultant reaction solution was separated into an organic phase and a water phase. The thus separated organic phase was washed with ion-exchanged water, filtered, concentrated and then purified by silica gel column chromatography to obtain 80 g of 2-methacryloyloxy-2-(3-(2-hydroxy-2-propyl)-1-adamantyl)propane as represented by the following formula (hereinafter referred to as "compound A"). The thus obtained compound A was identified by 1H-NMR and 13C-NMR (refer to FIGS. 1 and 2).; The synthesis of 2-methacryloyloxy-2-(3-(2-methacryloyloxy-2-propyl)-1-adamantyl)propane was performed by the following method. First, according to the method described in Japanese Patent Application Laid-open No. 2002-167342, 100 g of 1,3-dihydroxyadamantane was synthesized from adamantane. Next, a four-necked flask equipped with a stirrer, a thermometer, a dropping funnel and a Dimroth condenser was charged with 100 g of 1,3-dihydroxyadamantane, 500 mL of 1,2-dichloroethane and 800 g of 96percent sulfuric acid, and further 300 g of formic acid was dropped into the flask for 1 h. Thereafter, the contents of the flask were reacted at 25° C. for 10 h. The resultant reaction solution was filtered to separate precipitated crystals therefrom. The thus separated crystals were washed with water to obtain 140 g of <strong>[39269-10-8]1,3-adamantanedicarboxylic acid</strong>.Then, a four-necked flask equipped with a stirrer, a thermometer and a Dimroth condenser was charged with 140 g of <strong>[39269-10-8]1,3-adamantanedicarboxylic acid</strong>, 12 g of 96percent sulfuric acid, 200 g of methanol and 1000 mL of 1,2-dichloroethane, and the contents of the flask were reacted at 62° C. for 10 h. After completion of the reaction, the resultant reaction solution was separated into an organic phase and a water phase. The thus separated organic phase was washed with a saturated sodium hydrogencarbonate aqueous solution, and then concentrated. The obtained crystals were separated by filtration from the organic phase, thereby obtaining 150 g of methyl 1,3-adamantanedicarboxylate. Next, a four-necked flask equipped with a stirrer, a thermometer, a Dimroth condenser and a dropping funnel was charged with 100 g of methyl 1,3-adamantanedicarboxylate and 500 mL of tetrahydrofuran, and then 600 mL of a 3M magnesium methyl bromide/diethyl ether solution was dropped into the flask for 1 h. Thereafter, the contents of the flask were stirred at 25° C. for 3 h, and then mixed with water ...
  • 5
  • [ 39269-10-8 ]
  • [ 1459-95-6 ]
YieldReaction ConditionsOperation in experiment
95% With thionyl chloride; triethylamine; In methanol; N,N-dimethyl-formamide; Example 84 In an atmosphere of nitrogen, 10 mmole of 1,3-dicarboxyadamantane obtained by the method of Example 64 was dissolved in 10 ml of DMF. To the mixture, 30 mmole of thionyl chloride was added dropwise over 30 minutes and the mixture was heated to begin to reflux around the conclusion of addition. After refluxing for 2 hours, the mixture was cooled. To the mixture, 40 mmole of triethylamine was added followed by 22 mmole of methanol over 30 minutes while retaining the temperature of the mixture at 10°C or less, and then stirred for more 2 hours. As a result, the conversion of 1,3-dicarboxyadamantane was 99percent, and 1,3-bis(methoxycarbonyl)adamantane (yield 95percent) was formed. White solid Mass spectral data [M]+: 252 IR(cm-1): 1620, 1240, 1030
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