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Chemical Structure| 82654-98-6 Chemical Structure| 82654-98-6
Chemical Structure| 82654-98-6

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Vanillyl butyl ether, an ether of monohydroxybenzoic acid, is added to food products as a flavoring agent. It is also present in cosmetics and personal care products as a fragrance ingredient, oral care agent, hair conditioning agent, and warming or cooling agent.

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Product Details of Vanillyl butyl ether

CAS No. :82654-98-6
Formula : C12H18O3
M.W : 210.27
SMILES Code : OC1=CC=C(COCCCC)C=C1OC
MDL No. :MFCD00238529
InChI Key :VLDFMKOUUQYFGF-UHFFFAOYSA-N
Pubchem ID :5084146

Safety of Vanillyl butyl ether

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Vanillyl butyl ether

* 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 [ 82654-98-6 ]

[ 82654-98-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 109-09-1 ]
  • [ 201230-82-2 ]
  • [ 82654-98-6 ]
  • pyridine-2-carboxylic acid 4-butoxymethyl-2-methoxy-phenyl ester [ No CAS ]
  • 2
  • [ 498-00-0 ]
  • [ 71-36-3 ]
  • [ 82654-98-6 ]
YieldReaction ConditionsOperation in experiment
83% With sulfated tungstate; at 80℃; for 3h;Green chemistry; General procedure: Sulfated tungstate (10 wt%) was added to a mixture of p-methoxybenzyl alcohol (1 g, 7.25 mmol) and n-butanol (1.34 g, 18.11 mmol), and the reaction mixture was stirred at 80 C for 1 h. The progress of the reaction was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was diluted with EtOAc (15 ml) and filtered to recover the catalyst. The organic layer was concentrated under reduced pressure, and the residue obtained was purified by chromatography on silica gel (60-120) with n-hexane-EtOAc (90:10) as eluent to get pure p-methoxybenzyl ether as a colorless oil.
  • 3
  • [ 121-33-5 ]
  • [ 71-36-3 ]
  • [ 82654-98-6 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogen; at 20℃; under 7500.75 Torr; for 18h;Industrial scale; 1 kg of vanillin, 13.1 liters of n-butanol (vanillin concentration of 0.5 mol / L), 0.2 kg of catalyst A and 0. 05 kg of catalyst E were added to the reactor and charged with IMPa hydrogen, Heated to 20 C reaction 18h, the detection of vanillin reaction is complete, stop heating, until the reaction tank after cooling the catalyst, the catalyst directly dry and then use. The filtrate was subjected to rotary evaporation to excess excess butanol, To give vanillin butyl ether 1. 33 kg, yield 96%, purity> 98%.
68.55% 100.00 g of vanillin was dissolved in 243.59 g of n-butanol,Stirring and stirring, the metal catalyst Pb-C 2.97g was charged.Filled with 1.8MPa hydrogen, heated to 60 ~ 70 C reaction for 8 hours,The vanillin reaction is completely detected, the heating is stopped, and after the reaction liquid is cooled, the metal catalyst Pb-C is recovered by filtration, and the filtrate is put into the reaction tank.14.87 g of aluminum trichloride was added, and the temperature was raised to 60 to 70 C for 12 hours.After cooling to room temperature, the solid in the reaction liquid was removed by filtration, the residue was washed, and the washing liquid was combined with the filtrate, and the mixture was distilled under reduced pressure to obtain a crude colorless liquid.After washing with 100 g of water, the organic phase was separated and vacuum distilled at 165 C.94.74 g of vanillyl butyl ether was obtained in a yield of 68.55% and a purity of >98%.
  • 4
  • [ 109-69-3 ]
  • [ 121-33-5 ]
  • [ 82654-98-6 ]
YieldReaction ConditionsOperation in experiment
90.51% With potassium borohydride; In ethyl acetate; at 30 - 40℃; for 3h; 100.00 g of vanillin was dissolved in 231.65 g of ethyl acetate.Stir and dissolve, and add 28.36 g of potassium borohydride and 60.85 g of chlorobutane.The reaction was carried out at 30 to 40 C for 4 hours.After cooling to normal temperature, the solid in the reaction liquid was removed by filtration, and the residue was washed, and the washing liquid was combined with the filtrate, and the mixture was distilled under reduced pressure to obtain a crude colorless liquid.Vacuum distillation at 165 C,125.09 g of vanillyl butyl ether was obtained in a yield of 90.51% and a purity of >99%. This example differs from Example 1 in that the alkylating agent is chlorobutane and the rest are the same as in Example 1.
  • 5
  • [ 109-65-9 ]
  • [ 121-33-5 ]
  • [ 82654-98-6 ]
YieldReaction ConditionsOperation in experiment
98.13% With potassium borohydride; In ethyl acetate; at 30 - 40℃; for 3h; 100.00 g of vanillin was dissolved in 231.65 g of ethyl acetate.Stirring and stirring, and adding 28.36 g of potassium borohydride,108.07 g of bromobutane was reacted at 30 to 40 C for 3 hours.After cooling to normal temperature, the solid in the reaction liquid was removed by filtration, and the residue was washed, and the washing liquid was combined with the filtrate, and the mixture was distilled under reduced pressure to obtain a crude colorless liquid.Vacuum distillation at 165 C gave 135.62 g of vanillyl butyl ether in a yield of 98.13% and a purity of >99%. The difference between this embodiment and the embodiment 1 is that the reaction time is 3 hours.The molar ratio of vanillin to bromobutane was 1:1.2, and the others were the same as in Example 1.
 

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