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Chemical Structure| 23062-53-5 Chemical Structure| 23062-53-5
Chemical Structure| 23062-53-5

methyl 4-hydroxybicyclo[2.2.2]octane-1-carboxylate

CAS No.: 23062-53-5

4.5 *For Research Use Only !

Cat. No.: A197665 Purity: 97%

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Product Details of [ 23062-53-5 ]

CAS No. :23062-53-5
Formula : C10H16O3
M.W : 184.23
SMILES Code : O=C(C1(CC2)CCC2(O)CC1)OC
MDL No. :MFCD18837585
InChI Key :LUBWUSMZFMBOIQ-UHFFFAOYSA-N
Pubchem ID :12560142

Safety of [ 23062-53-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 23062-53-5 ]

* 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 [ 23062-53-5 ]

[ 23062-53-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 186581-53-3 ]
  • [ 1127-13-5 ]
  • [ 23062-53-5 ]
  • 2
  • [ 1127-13-5 ]
  • [ 18107-18-1 ]
  • [ 23062-53-5 ]
YieldReaction ConditionsOperation in experiment
99% In methanol; hexane; at 20℃; for 2h; To a solution of 4-hydroxy-bicyclo [2. 2. 2] OCTANE-1-CARBOXYLIC acid (0. 10 g, 0. 59 mmol) in methanol (5 mL), was slowly added a solution of (trimethylsilyl) diazomethane in hexane (2. 0 M, 1 mL). The reaction mixture was stirred for 2 hours at room temperature. Solvent was then removed to give 4-hydroxy- bicyclo [2. 2. 2] octane-1-carboxylic acid methyl ester as a yellow solid (0. 105 g, 99%). H NMR (300 MHz, CDC13, 5) : 3. 56 (s, 3H), 1. 85 (m, 6H), 1. 59 (m, 6H).
89% In methanol; dichloromethane; at 20℃; To a 500 mL round-bottom flask was added 4-hydroxybicyclo[2.2.2]octane-l-carboxylic acid 58d (15.5 g, 91.07 mmol, 1.0 equiv.), dichloromethane (85 mL), methanol (45 mL), and TMSCHN2 (85 mL, 2.0 equiv.). The resulting mixture was stirred overnight at RT, then concentrated in vacuo. The crude product was purified by Flash-Prep-HPLC using the following conditions: Column, silica gel; mobile phase, PE:EtOAc = 100:0 increasing to PE:EtOAc =:: 90: 10 within 20 min; Detector, UV 254 nm, yielding methyl 4-hydroxybicyclo[2.2.2]octane-l- carboxylate 58e (15 g, 89%) as a white solid.
  • 3
  • [ 1127-13-5 ]
  • [ 74-88-4 ]
  • [ 23062-53-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; To a mixture of compound 16a (1.2 g, 7.05 mmol) and K2CO3(1.5 g, 10.85 mmol) in DMF (20 mL) was added MeI (1.5 g, 10.57 mmol) dropwise over 5 min. The mixture was stirred at room temperature overnight, quenched with water (20 mL) and extracted with EtOAc (30 mL x 3) . The combined organic layers were washed with brine (30 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford crude compound 16b (1.2 g, 92yield) as a yellow solid, which was used to the next step without further purification.1H NMR (DMSO-d6, 400 MHz) : delta 4.34 (s, 1H) , 3.55 (s, 3H) , 1.81-1.75 (m, 6H) , 1.53-1.48 (m, 6H) .
 

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