Ethyl Vanillate | Bourbonal | Benzene Compounds

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Quality Control of Ethyl Vanillate Purity: 98% SDS Specification

COA

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NMR

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CNMR

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Product Details of Ethyl Vanillate

CAS No. :	617-05-0
Formula :	C₁₀H₁₂O₄
M.W :	196.20
SMILES Code :	CCOC(=O)C1=CC(OC)=C(O)C=C1
Synonyms :	Bourbonal; Ethylprotal
MDL No. :	MFCD00017269
InChI Key :	MWAYRGBWOVHDDZ-UHFFFAOYSA-N
Pubchem ID :	12038

Safety of Ethyl Vanillate

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Ethyl Vanillate

* 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 [ 617-05-0 ]

[ 617-05-0 ] Synthesis Path-Downstream 1~35

1
[ 917-64-6 ]
[ 617-05-0 ]
[ 51941-34-5 ]

References: [1]Bulletin de la Societe Chimique de France,1908,vol. <4> 3,p. 730.
Bulletin de la Societe Chimique de France,1910,vol. <4> 7,p. 332.

2
[ 64-17-5 ]
[ 121-34-6 ]
[ 617-05-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sulfuric acid; for 48h;Inert atmosphere; Reflux;	Synthesis of ethyl 4-hydroxy-3-methoxybenzoate: In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, a solution of vanillic acid (10 g, 59.49 mmol) in EtOH (400 mL) was added. To the above solution 600 mg (6.11 mmol) of cone. H2SO4 was added. The mixture was then stirred at reflux temperature for 48 h. The solution was rotary evaporated. Water (100 mL) was then added to the residue and the separated greenish oil was then removed by using separately funnel. Product was then dried in vacuo to obtain 11.45 g (98 %) of ethyl 4-hydroxy-3-methoxybenzoate. 1H NMR (400 MHz, Chloroform-d) delta 7.62 (dd, J= 8.5, 2.1 Hz, 1H), 7.53 (d, J= 1.8 Hz, 1H), 6.91 (d, J= 8.6 Hz, 1H), 4.33 (q, J= 7.1 Hz, 2H), 3.91 (s, 3H), 1.36 (t, J= 7.3 Hz, 3H). HPLC-MS: Expected: 197 (MH+); Found: 197.
98%	With sulfuric acid; for 48h;Reflux; Inert atmosphere;	In a round bottomed flask equipped with a nitrogen inlet and a magnetic stir bar, a solution of 4-hydroxy-3- methoxybenzoic acid (10 g, 59.49 mmol) in EtOH (400 mL) was added. To the above solution 600 mg (6.11 mmol) of cone. H2SO4 was added. The mixture was then stirred at reflux temperature for 48 h. The solution was rotary evaporated. Water (100 mL) was then added to the residue and a greenish oily compound separates out. The greenish oil was then separated and then dried in vacuo to 11.45 g (98 %) of ethyl 4-hydroxy-3- methoxybenzoate. (0284) 1H NMR (400 MHz, Chloroform-d) delta 7.62 (dd, J = 8.5, 2.1 Hz, 1H), 7.53 (d, J = 1.8 Hz, 1H), 6.91 (d, J = 8.6 Hz, 1H), 4.33 (q, J = 7.1 Hz, 2H), 3.91 (s, 3H), 1.36 (t, J = 7.3 Hz, 3H). HPLC-MS: Expected: 197 (MH+); Found: 197
	With sulfuric acid; for 10h;Reflux;	4-Hydroxy-3-methoxybenzoic acid (20 g, 119 mmol) in ethanol (50 mL) was treated with concentrated sulfuric acid (3 mL) under reflux for 10 h. The solvent was evaporated until no longer liquid outflow. Water (20 mL) was added, extracting by adding respectively 30 mL ethyl acetate. After washing the organic phase with saturated NaCl solution (40 mL), drying it with anhydrous Na2SO4 and evaporating the solvent under reduced pressure. Crude product were purified by column chromatography, product 2 appeared.

	With hydrogenchloride; at 60℃; for 14h;	[0573j To a solution of 4-hydroxy-3-methoxybenzoic acid (6-A) (5 g, 29.7 mmol) in EtOH (20 mL) was added HC1. The mixture was stirred for 60C for 14 h. The reaction was concentrated to afford crude ethyl 4-hydroxy-3-methoxybenzoate (6-B) (4.6 g, 79% yield).
	With sulfuric acid; In water; for 6h;Reflux;	General procedure: Hydrazides (30-58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3-6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).

References: [1]Patent: WO2017/62804,2017,A1 .Location in patent: Paragraph 0070.
[2]Patent: WO2018/144900,2018,A1 .Location in patent: Page/Page column 47-48.
[3]International Journal of Pharmacy and Pharmaceutical Sciences,2019,vol. 11,p. 85 - 91.
[4]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4279 - 4290.
[5]Chemische Berichte,1877,vol. 10,p. 60 Anm..
[6]Molecular Crystals and Liquid Crystals (1969-1991),1982,vol. 99,p. 279 - 284.
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 526 - 531.
[8]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4226 - 4236.
[9]MedChemComm,2013,vol. 4,p. 827 - 832.
[10]Patent: WO2014/31784,2014,A1 .Location in patent: Paragraph 0573.
[11]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6014 - 6024.
[12]New Journal of Chemistry,2016,vol. 40,p. 6977 - 6985.
[13]Green Chemistry,2018,vol. 20,p. 3214 - 3221.

3
[ 617-05-0 ]
[ 2008-75-5 ]
[ 101867-16-7 ]

References: [1]Monatshefte fur Chemie,1957,vol. 88,p. 1064,1066, 1067.

4
[ 617-05-0 ]
[ 119682-53-0 ]
phosphoric acid bis-(4-ethoxycarbonyl-2-methoxy-phenyl ester) [ No CAS ]

References: [1]Gazzetta Chimica Italiana,1957,vol. 87,p. 519,524.

5
[ 617-05-0 ]
[ 100377-63-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With hydrazine hydrate; In ethanol; water;Reflux;	General procedure: Hydrazides (30-58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3-6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).
	With hydrazine hydrate; In ethanol; for 20h;Reflux;	A stirred solution of compound 2 (50 mmol) in ethanol (50 mL) was treated with 85% hydrazine hydrate (20 mL), under reflux for 20 h. After cooling, removal of the solvent under reduced pressure gave a crude product, which was filtered off and purified by washing with saturated NaCl (40 mL) together with small quantity of ethanol to give compound 3.

References: [1]International Journal of Pharmacy and Pharmaceutical Sciences,2019,vol. 11,p. 85 - 91.
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6014 - 6024.
[3]Chemische Berichte,1926,vol. 59,p. 733.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 526 - 531.
[5]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 838 - 845.
[6]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4226 - 4236.
[7]Polymer,2016,vol. 99,p. 83 - 89.

6
[ 617-05-0 ]
[ 106-93-4 ]
[ 100388-19-0 ]

References: [1]Monatshefte fur Chemie,1957,vol. 88,p. 1064,1066, 1067.
[2]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 2569 - 2572.

7
[ 617-05-0 ]
[ 100-35-6 ]
[ 101450-57-1 ]

References: [1]Monatshefte fur Chemie,1957,vol. 88,p. 1064,1066, 1067.

8
[ 617-05-0 ]
[ 107-05-1 ]
[ 119870-95-0 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1943,vol. 63,p. 155.
Chem.Abstr.,1951,p. 2907.

9
[ 617-05-0 ]
[ 106-89-8 ]
[ 63477-29-2 ]

References: [1]Patent: DE819698,1950, .
DRP/DRBP Org.Chem.,.

10
[ 617-05-0 ]
[ 572-09-8 ]
[ 114277-88-2 ]

References: [1]Journal Of Scientific and Industrial Research,1959,vol. 18 B,p. 522,524.
[2]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 2056 - 2064.

11
[ 600-00-0 ]
[ 617-05-0 ]
2-Methyl-2-(4-hydroxy-3-methoxy-benzoyl)-propionsaeure-aethylester [ No CAS ]

References: [1]Gazzetta Chimica Italiana,1963,vol. 93,p. 451 - 454.

12
[ 617-05-0 ]
[ 4584-46-7 ]
[ 92324-37-3 ]

References: [1]Patent: GB919126,1959, .
Chem.Abstr.,1963,vol. 59.

13
[ 1847-84-3 ]
[ 35030-98-9 ]
[ 617-05-0 ]

References: [1]Journal of Organic Chemistry,1972,vol. 37,p. 3160 - 3163.

14
[ 1847-84-3 ]
[ 617-05-0 ]

References: [1]Journal of Organic Chemistry,1972,vol. 37,p. 3160 - 3163.

15
[ 617-05-0 ]
[ 100-44-7 ]
[ 185033-64-1 ]

References: [1]Molecular Crystals and Liquid Crystals (1969-1991),1982,vol. 99,p. 279 - 284.

16
[ 617-05-0 ]
[ 141-43-5 ]
[ 5942-25-6 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 383 - 388.

17
[ 617-05-0 ]
[ 109-64-8 ]
4-(3-Bromo-propoxy)-3-methoxy-benzoic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1119 - 1131.

18
[ 121-34-6 ]
[ 75-03-6 ]
[ 617-05-0 ]

References: [1]Synthetic Communications,1998,vol. 28,p. 2021 - 2026.

19
[ 92-66-0 ]
[ 617-05-0 ]
[ 158771-41-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1999,vol. 47,p. 1073 - 1080.

21
[ 700-16-3 ]
[ 617-05-0 ]
[ 199784-56-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 657 - 666.
[2]Patent: US6350746,2002,B1 .Location in patent: Page column 35.

22
[ 121-34-6 ]
[ 78-39-7 ]
[ 617-05-0 ]

References: [1]Synthetic Communications,2002,vol. 32,p. 2209 - 2213.

23
[ 617-05-0 ]
diethyl 6,6'-dihydroxy-5,5'-dimethoxybiphenyl-3,3'-dicarboxylate [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,2003,vol. 68,p. 1515 - 1530.

24
[ 262447-61-0 ]
[ 617-05-0 ]
[ 859831-57-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4279 - 4290.

25
[ 617-05-0 ]
[ 69610-40-8 ]
[ 922529-62-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,2006,vol. 54,p. 1515 - 1529.

26
[ 617-05-0 ]
[ 106-95-6 ]
[ 119870-95-0 ]

References: [1]Canadian Journal of Chemistry,2007,vol. 85,p. 66 - 76.

27
[ 617-05-0 ]
ethyl 3-methoxy-4-(3-propyltriethoxysilyl)benzoate [ No CAS ]

References: [1]Canadian Journal of Chemistry,2007,vol. 85,p. 66 - 76.

28
[ 617-05-0 ]
4-[2-(9H-carbazol-4-yloxy)-ethoxy]-3-methoxy-benzoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4279 - 4290.

29
[ 617-05-0 ]
[ 426826-63-3 ]