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Chemical Structure| 62501-72-8 Chemical Structure| 62501-72-8

Structure of 62501-72-8

Chemical Structure| 62501-72-8

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Product Details of [ 62501-72-8 ]

CAS No. :62501-72-8
Formula : C9H10O3
M.W : 166.17
SMILES Code : OC[C@@H]1COC2=CC=CC=C2O1
MDL No. :MFCD11519093

Safety of [ 62501-72-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 62501-72-8 ]

* 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 [ 62501-72-8 ]

[ 62501-72-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 70918-54-6 ]
  • [ 62501-72-8 ]
YieldReaction ConditionsOperation in experiment
85% With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃;Inert atmosphere; General procedure: A solution of (R)-methyl 1,4-benzodioxan-2-carboxylate (R)-17a (1 mmol) in anhydrous THF (10 mL) was slowly added under a nitrogen atmosphere, to a suspension of LiAlH4 (2 mmol) in anhydrous THF (50 mL). The mixture was stirred at room temperature until the completion of the reaction as indicated by TLC. After hydrolysis with small amounts of water, the suspension obtained was filtered and the THF removed. The residue was diluted with water and extracted with ether. The organic layers were dried, filtered, and concentrated to obtain pure alcohol ( S)- 2 after recrystallization from diethyl ether, in 85% yield as a white solid
  • 2
  • [ 62501-72-8 ]
  • [ 70918-54-6 ]
YieldReaction ConditionsOperation in experiment
85% (R)-1,4-benzenedioxane-2-methanol (100 g, 0.6 mol) was dissolved in dichloromethane (1 L).Add potassium bromide aqueous solution (14 g, 0.12 mol, water 500 mL),Tempo (1.8 g, 0.012 mol), aqueous potassium hydrogencarbonate (120 g, 1.2 mol),Stir for 10 minutes after the addition.The reaction system was cooled to 0-5 C in an ice bath.Slowly add sodium hypochlorite aqueous solution (10%, 860 mL).Keep the temperature of the system below 10 C, keep the temperature for 3 hours after the completion of the dropwise addition, naturally heat up, and react at room temperature for another 10 hours.After completion of the reaction, excess sodium hypochlorite was quenched with aqueous sodium thiosulfate (74 g, 0.3 mol, water 100 mL). The reaction system is adjusted to a pH greater than 12 with a 50% aqueous sodium hydroxide solution.Layered,The aqueous phase was extracted once more with dichloromethane. Divide twice the dichloromethane. The aqueous phase is adjusted to pH less than 2 with hydrochloric acid, then extracted three times with dichloromethane, and the organic phase is combined three times.Dry and concentrated,That is, 92 g of the target (S)-1,4-benzodioxane-2-carboxylic acid was obtained in a yield of 85%.
With potassium permanganate; potassium hydroxide; In water; acetone; at 0℃; for 0.5h; General procedure: The alcohol (S)-2 (0.4 g, 3.0 mmol) dissolved in acetone (3 mL) was added to an aqueous solution (containing KOH, 0.18 g in 40 mL H2O). A solution of aqueous KMnO4 (50%) was added dropwise at 0C with stirring until the color of permanganate was retained for 30 min. After the consumption of the starting material, the excess permanganate was decomposed by the dropwise addition of MeOH. Solvents were evaporated to dryness, the residue suspended in dichloromethane (3x30 mL) and acidified with 10% HCl. The organic solvent was removed under reduced pressure to obtain the desired acid in 70% yield as a white solid.
 

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