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CAS No. : | 2955-46-6 | MDL No. : | MFCD11036946 |
Formula : | C11H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IQJSVQFIOUFWMU-UHFFFAOYSA-N |
M.W : | 194.23 | Pubchem ID : | 257579 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With water; potassium hydroxide In ethylene glycol at 150℃; for 7 h; | Step 24b: 2-(4-Methoxyphenyl)-2-methylpropanoic acid (Compound 0803-27)To a solution of 2-(4-Methoxyphenyl)-2-methylpropanenitrile (compound 0802- 27) (1.63 g, 9.30 mmol) in ethylene glycol (3.40 mL) was added potassium hydroxide (1.29 g, 22.99 mmol) and water (0.46 mL). The reaction mixture was heated at 150°C for 7 h. The mixture was poured into water, adjusted to pH 2 with <n="79"/>concentrated hydrochloric acid. The mixture was filtered and the collected solid was washed with water and dried in vacuum to afford product 0803-27 (0.85 g, 47 percent) as a white solid: LCMS: 195 [M+l]+. 1H NMR (DMSO-d6): δ 1.44 (s, 6H), 3.73 (s, 3H), 6.88 (d, J= 9.2 Hz, 2H), 7.25 (d, J= 8.4 Hz, 2H), 12.23 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: With potassium hydroxide In water; ethylene glycol at 20 - 160℃; Stage #2: With hydrogenchloride In monoethylene glycol diethyl ether; water |
A mixture of 2- (4-methoxyphenyl)-2-methylpropionitrile g, 2.04 mol), KOH (284.8 g, 5.08 mol), ethylene glycol (750 mL), and water (100 mL) was heated at 150-160 °C for 7 h in a 1L round-bottom flask equipped with a bump flask and fermentation lock, then allowed to cool and stand overnight. Heating was continued for an additional 7 hours, without any additional conversion being observed. The reaction was allowed to cool and poured into water (2 L), then acidified with stirring to pH 10-11 by addition of concentrated HCI (-250 mL). The resulting solution was extracted with isopropyl acetate (1x1 L, followed by 2x500 mL) and then filtered to remove a small quantity of a white precipitate. The reaction mixture was stirred vigorously and slowly acidified further to ca pH = 2 with concentrated HCl (-250 mL). The product started to precipitate at pH 6-7. The suspension was stirred for 30 minutes at ambient temperature then kept a refrigerator overnight. The mixture was filtered and the precipitate was washed with cold 1M HCl (500 mL), followed cold water (2x150 mL). The solid was dried under suction, follow by high vacuum (lyophilizer) overnight to give 2- (4-methoxyphenyl)-2-methylpropanoic (314 g, 80percent) as pale yellow-orange crystals containing approximately 2.0 percent of the mono-methyl impurity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | at 20 - 180℃; for 5 - 23 h; | Step 4 a,a-Dimethyl 4-methoxyphenylacetic acid (108 g; 0.556 mol) was heated with pyridineNo.HCl (324 g; 2.80 mol) to 180 °C for 5 hours. The reaction mixture was allowed to cool to ca 90 °C, then added to an equal volume of 10percent aqueous sodium hydroxide and chipped ice to give a basic solution. The aqueous solution was washed with diethyl ether, then acidified to pH = 3 with 85percent H3P04. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were concentrated in vacuo to give a solid, which was recrystallized from water to give a,a-dimethyl 4-hydroxyphenylacetic acid. Alternate procedure a,a-Dimethyl 4-methoxyphenylacetic acid (100 g; 0.515 mol) and pyridineNo.HCl (297 g; 2.57 mol) were heated with stirring at 180 °C for 5 hours. The reaction mixture was allowed to cool to room temperature and then stand overnight. After 18 hours, the reaction was re-heated such that it was homogeneous for the purpose of sampling and then cooled to ~100°C and poured onto a mixture of 1L chipped-ice and 10percent aqueous NaOH (1.5 L). The aqueous layer was extracted with diethyl ether, then acidified with 85percent aqueous H3P04 to pH = 3 (@130 mL), and then extracted with EtOAc (500 mL, followed by 250 mL). The combined organic extracts were concentrated in vacuo to give a solid, which was crystallized from hot water. Once crystals had significantly established stirring was started at a rate so as to maintain mobility of the entire precipitate and then continued overnight. The mixture was cooled in a fridge for 2 hours prior to collection of the crystals by filtration. The crystals were washed with a minimum amount of cold water (~100 mL), and then dried, first under suction and then under high vacuum (lyophilizer) to give a,a-dimethyl 4- hydroxyphenylacetic acid (76.3 g, 82percent) as a tan crystalline solid. |
76% | at 180℃; for 5 h; | Step 24c: 2-(4-Hydroxyphenyl)-2-methylpropanoic acid (Compound 0804-27)A mixture of 2-(4-Methoxyphenyl)-2-methylpropanoic acid (compound 0803- 27) (0.85 g, 4.38 mmol ) and pyridine hydrochloride (2.82 g, 24.40 mmol) was heated at 180°C for 5 h, The reaction mixture was then cooled to room temperature and adjusted to pH 6 with dilute hydrochloric acid (1 M) and extracted with ethyl acetate. The organic layer was separated, dried over Na2SO4, and concentrated to afford desired product 0804-27 (0.61 g, 76 percent) as a colorless oil: LCMS: 181 [M+l]+. 1H NMR (400 MHz, DMSO-d6): δ 1.41 (s, 6H), 6.70 (d, J= 8.8 Hz, 2H), 7.13 (d, J= 8.8 Hz, 2H), 9.28 (s, IH), 12.16 (s, IH). |
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