Alternatived Products of [ 19728-20-2 ]
Product Details of [ 19728-20-2 ]
| CAS No. : | 19728-20-2 |
MDL No. : | MFCD01365737 |
| Formula : |
C12H16O3
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
208.25
|
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 19728-20-2 ]
| Signal Word: | |
Class: | |
| Precautionary Statements: | |
UN#: | |
| Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 19728-20-2 ]
* 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 [ 19728-20-2 ]
- 1
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[ 499-75-2 ]
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[ 79-11-8 ]
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[ 19728-20-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 82% |
Stage #1: carvacrol With sodium hydroxide In water monomer at 50℃; for 0.5h;
Stage #2: chloroacetic acid In water monomer at 50℃;
Stage #3: With sulfuric acid |
Phenoxy Acid Synthesis
General procedure: A phenol compound (thymol, carvacrol, eugenol, vanilin) dissolved in warm waterwas added to a solution of sodium hydroxide (2.1 eq.) in warm water. After mixing for30 min at 50 C, monochloroacetic acid (2.1 eq.) was added. The obtained solution wasmixed overnight at 50 C. After cooling to room temperature, the solution was acidified topH 2 with 10% sulfuric acid. The obtained solid phenoxy acetic acid was separated witha Buchner funnel. Water from the aqueous phase was removed on a rotary evaporator,and the residue was dissolved in hot toluene and washed with water. After separationfrom the organic phase, phenoxyacetic acid was precipitated and separated with a Buchnerfunnel. The combined crude phenoxyacids were dissolved in hot toluene, and activatedcharcoal was added and mixed for 15 min at 50 C. After removing the charcoal from thehot solution, the organic phase was cooled to room temperature, and the obtained solidphenoxyacetic acid was filtrated and dried in vacuum. |
| 62% |
With sodium hydroxide for 0.0166667h; microwave irradiation; |
|
| 45% |
With sodium hydroxide In water monomer at 120℃; for 3h; Inert atmosphere; |
|
| 45% |
Stage #1: carvacrol; chloroacetic acid With sodium hydroxide In water monomer at 120℃; for 3h; Heating / reflux;
Stage #2: With hydrogenchloride In water monomer at 20℃; |
4
NaOH beads (66.6 mmol), dissolved in water were added to a mixture of carvac- rol 9 (33.3 mmol), chloroacetic acid 10 (33.3 mmol) and water (50 ml). The mixture was refluxed at 120 0C for 3 h. The mixture was cooled to room temperature and acidified with hydrochloric acid. The crude product was extracted with di- ethyl ether and washed with water. The solvent was evaporated, thus giving car- vacrol oxyacetic acid 11 (yield: 83 %). The crude product was purified by dissolving in diethyl ether, followed by extraction with water and NaHCO3 solution. Aqueous phases were pooled, acidified with hydrochloric acid and extracted with diethyl ether. The ether phase was dried, followed by evaporation of the solvent to dryness, thus giving carvacrol acetic acid 11 (yield: 45 %). Betulin 1 (7.2 mmol) and carvacrol oxyacetic acid 11 (7.2 mmol) were weighed into a flask, and toluene (80 ml) was added. The bath was heated to 160 0C3 and then isopropyl titanate (1.4 mmol) was added. The reaction mixture was refluxed for 6 h untill all water was separated by the water separation tube. The mixture was cooled to room temperature and the precipitate formed was filtered. The organic phase was washed with NaHCO3 solution and the solvent was evaporated. The crude product was recrystallized from boiling solution of cyclohexane and toluene. The solvent was evaporated to dryness, thus isolating 28-carboxymethoxy carvacrolester of betulin 12 (yield: 55 %) as the reaction product. |
| 45% |
Stage #1: carvacrol; chloroacetic acid With sodium hydroxide In water monomer at 120℃; for 3h; Heating / reflux;
Stage #2: With hydrogenchloride In water monomer at 20℃; |
4
NaOH beads (66.6 mmol), dissolved in water, were added to a mixture of carvao rol 9 (33.3 mmol), chloroacetic acid 10 (33.3 mmol) and water (50 ml). The mixture was refluxed at 120 0C for 3 h. The mixture was cooled to room temperature and acidified with hydrochloric acid. The crude product was extracted with di- ethyl ether and washed with water. The solvent was evaporated, thus giving car- vacrol oxyacetic acid 11, yield 83 %. The crude product was purified by dissolving in diethyl ether, followed by extraction with water and NaHCO3 solution. Aqueous phases were pooled, acidified with hydrochloric acid and extracted with diethyl ether. The ether phase was dried followed by evaporation of the solvent to dryness, thus giving carvacrol acetic acid 11, yield 45 %. Betulin 1 (7.2 mmol) and carvacrol oxyacetic acid 11 (7.2 mmol) were weighed into a flask and toluene (80 ml) was added. The bath was heated to 160 0C and isopropyl titanate (1.4 mmol) was added. The reaction mixture was refluxed for 6 h until all water was separated by water separation tube. The mixture was cooled to RT and the precipi- tate formed was filtered. The organic phase was washed with NaHCO3 solution and the solvent was evaporated. The crude product was recrystallized from boiling solution of cyclohexane and toluene. The solvent was evaporated to dryness, thus isolating 28-carboxymethoxy carvacrolester of betulin 12 yield 55 %. |
|
With alkali |
|
|
With sodium hydroxide |
|
Reference：
[1]Bojko, Barbara; Jaroch, Karol; Karolak, Maciej; Krysiński, Jerzy; Materna, Katarzyna; Pałkowski, Łukasz; Podemski, Jonasz; Skrzypczak, Andrzej; Walkiewicz, Filip; Wojcieszak, Marta
[Molecules, 2022, vol. 27, # 6]
[2]Nagy, Gabriela; Filip, Sorin V.; Surducan, Emanoil; Surducan, Vasile
[Synthetic Communications, 1997, vol. 27, # 21, p. 3729 - 3736]
[3]Pohjala, Leena; Alakurtti, Sami; Ahola, Tero; Yli-Kauhaluoma, Jari; Tammela, Paeivi
[Journal of Natural Products, 2009, vol. 72, # 11, p. 1917 - 1926]
[4]Current Patent Assignee: VTT TECHNICAL RESEARCH CENTRE OF FINLAND - WO2007/141389, 2007, A1
Location in patent: Page/Page column 57-58
[5]Current Patent Assignee: VTT TECHNICAL RESEARCH CENTRE OF FINLAND - WO2007/141383, 2007, A1
Location in patent: Page/Page column 32-33
[6]Spica
[Gazzetta Chimica Italiana, 1880, vol. 10, p. 345]
[7]Koelsch
[Journal of the American Chemical Society, 1931, vol. 53, p. 304]
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