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Chemical Structure| 29412-62-2 Chemical Structure| 29412-62-2

Structure of 29412-62-2

Chemical Structure| 29412-62-2

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Product Details of [ 29412-62-2 ]

CAS No. :29412-62-2
Formula : C12H12O4
M.W : 220.22
SMILES Code : O=C(C12C3C4C5(C(OC)=O)C3C1C5C24)OC
MDL No. :MFCD00192075
InChI Key :OXBMFCGRQJNAOY-UHFFFAOYSA-N
Pubchem ID :141480

Safety of [ 29412-62-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319-H315-H335
Precautionary Statements:P302+P352-P280-P305+P351+P338-P261

Application In Synthesis of [ 29412-62-2 ]

* 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 [ 29412-62-2 ]

[ 29412-62-2 ] Synthesis Path-Downstream   1~4

  • 2
  • [ 29412-62-2 ]
  • [ 32846-66-5 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 14h;Inert atmosphere; A 2.5 M solution of NaOH in MeOH (7.60 mL, 19.1 mmol, 1.05 equiv.) was added dropwise to a solution of 27 (4.00 g, 18.2 mmol) in THF (125 mL) at rt. The mixture was stirred for 14 h and the solvent evaporated in vacuo without heating. The residue was diluted with H2O (45 mL) and extracted with CHCl3 (3 × 15 mL). The aqueous layer was acidified to pH 3 with 32% aq. HCl, extracted with CHCl3 (1 × 60 mL, 2 × 35 mL), and the combined organic layers dried (MgSO4). The solvent was evaporated under reduced pressure to give 28 as a colourless crystalline solid (3.46 g, 92%) with spectroscopic properties matching those previously reported:3 m.p. 183-184.5 C; (lit. m.p.3 182-183 C); 1H NMR (200.1 MHz, CDCl3); delta 4.30-4.24 (6H, m, CH), 3.72 (3H, s, CH3).
70% Cubane-1 ,4-dicarboxylic acid dimethyl esther(Pharmatech International Inc.) (3.10 g, 14.1 mmol) is dissolved in 15 ml of hot methanol in a 250 ml in a round-bottomed flask equipped with a condenser. Solid reagent NaOH (0.560 g, 14.1 mmol) is added, and the reaction mixture is heated under refluxed for a 13-15 hr period. The reaction mixture is then cooled to room temperature. The reaction mixture is diluted with 120 ml of water and extracted 3 times with 50 ml portions of ether, which is discarded.. The aqueous portion is acidified to ca. pH 3 with 6N HCl and then extracted with chloroform (4 portions of ca. 50 ml each). The combined chloroform extracts are dried and reduced by rotary evaporation to produce the diacid as an off-white powder in 70% yield.
With water; sodium hydroxide; Dimethyl cubane-1,4-dicarboxylate (3a) was prepared according to a known literature method.25 The diester was converted to the diacid upon treatment with NaOH/H2O, then precipitated with HCl/H2O, and washed thoroughly with distdwater. The diacid was recrystallized twice from glacial acetic acid, and was dried in vacuo prior to use. Compound 6 is a white powder. deltaH (250MHz, DMSO-d6): 4.10 (s, 6H). deltaC (62.5MHz, DMSO-d6): 172.7 (2C, carbonyl), 55.8 (2C, quaternary), 46.3 (6C, CH).
  • 3
  • [ 29412-62-2 ]
  • [ 24539-28-4 ]
  • [ 32846-66-5 ]
  • 4
  • [ 32846-66-5 ]
  • [ 29412-62-2 ]
YieldReaction ConditionsOperation in experiment
71% With Dowex 50W-X8 resin; In methanol; for 24h;Reflux; A solution of S5 (14.9 g, 77.4 mmol) in methanol (385 mL) was treated with dry methanol-washed Dowex 50W-X8 resin (1.82 g) and heated at reflux for 24 h. The hot reaction mixture was filtered and the solvent evaporated. The obtained solid was passed through a plug of silica gel eluting with CH2Cl2-methanol (95:5), and the filtrate evaporated in vacuo. The crude product was twice recrystallised from methanol to give 20 as off-white crystals (12.0 g, 71%), where the spectroscopic properties matched those previously described:1 mp 161-162 C; (lit. mp1 161-162 C); deltaH (200 MHz; CDCl3) 4.23 (6 H, s), 3.70 (6 H, s).
 

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