Structure of 1077-58-3
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CAS No. : | 1077-58-3 |
Formula : | C11H14O2 |
M.W : | 178.23 |
SMILES Code : | CC(C)(C)C1=C(C=CC=C1)C(O)=O |
MDL No. : | MFCD09258829 |
InChI Key : | ZDFKSZDMHJHQHS-UHFFFAOYSA-N |
Pubchem ID : | 136850 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
With sulfuric acid; potassium nitrate; at 0℃; | Compound 44b was dissolved in concentrated H2SO4 (25 mL) and cooled to 0 C. Then a solutionof KNO3 (20 mmol) in concentrated H2SO4 (25 mL) was dropwise added to the mixture. The mixturewas reacted at 0 C until the reaction was completed, and dropwise added to ice water. The resultedmixture was filtered and washed with water. The filter cake was dried and crystallized from EtOHto give intermediate 44b in yield of 40% over two steps. 1H-NMR (DMSO-d6): 13.75 (s, 1H), 8.21(dd, J = 8.8, 2.8 Hz, 1H), 8.10 (d, J = 2.8 Hz, 1H), 7.80 (d, J = 8.8 Hz, 1H), 1.43 (s, 9H) ppm; 13C-NMR(DMSO-d6): 170.88, 153.99, 144.99, 135.54, 128.88, 123.82, 122.76, 36.35, 30.62 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
942 mg | To a solution of <strong>[1077-58-3]2-tert-butylbenzoic acid</strong> (1.00 g) in THF(20 mL) was added 1.0M borane THF complex THF solution (16.8 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere, IN aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (942 mg) .XH NMR (300 MHz, DMSO-d6) δ 1.35 (9H, s) , 4.70 (2H, d, J = 5.4 Hz), 5.10 (1H, t, J = 5.4 Hz), 7.12-7.22 (2H, m) , 7.27-7.34 (1H, m) , 7.48-7.55 (1H, m) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrachloromethane; thionyl chloride; dichloromethane; | A solution of <strong>[1077-58-3]2-tert-butylbenzoic acid</strong> (4.0 g, 22.5 mmol) in thionyl chloride (8.2 mL, 112 mmol) was stirred at RT for 2 h, then was concentrated three times from carbon tetrachloride to remove all traces of excess thionyl chloride. A solution of diethylamine (4.93 g, 67.4 mmol) in CH2 Cl2 (10 mL) was added dropwise over 10 min to an ice water-cooled solution of the crude acid chloride in CH2 Cl2 (35 mL). Ten min after addition was complete, the reaction was partitioned between ether and 10% HCl. The ether phase was then washed with sat aq NaHCO3, then was dried (MgSO4), and concentrated to afford a quantitative yield of N,N-diethyl-2-tert-butylbenzamide as an off-white solid. m.p. 38.5-40.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With thionyl chloride; In methanol; toluene; | EXAMPLE 186 2-(1,1-Dimethylethyl)-N-ethyl-N-(1-methoxy-2,2-dimethylpropyl)benzamide A mixture of <strong>[1077-58-3]2-tert-butylbenzoic acid</strong> (15.7 g, 88.2 mmol) and thionyl chloride (19.3 mL, 265 mmol) was stirred at RT for 1 day, then was concentrated and stripped from toluene (2*) under vacuum. The compound from example k (19.94 g, 176.5 mmol) was added to a solution of this crude 2-tert-butylbenzoyl chloride in toluene (90 mL), and the mixture was heated at 100 C. for 3 h, then was stirred at room temperature overnight. The resulting mixture was cooled with an ice-water bath, and Et3 N (13.4 g, 132.4 mmol) was added, followed by the dropwise addition of methanol (5.65 g, 176.6 mmol). The resulting reaction mixture was stirred at RT and monitored to completion by GLC, then was partitioned between ether and sat aq NaHCO3. The ether extract was dried (MgSO4), concentrated, and purified by flash chromatography with 1:9 EtOAc/hexanes to afford 20.8 g of the title compound as a pale yellow oil, a 77% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium hydroxide; In dimethyl sulfoxide; | N-methyl-N-[2-(2-tert-butylphenylcarboxy)-1,1-dimethylethyl]trifluoromethanesulfonamide (1 eq) was saponified in a 2.0M solution of KOH (3 eq) in DMSO at 110 C. for 4 h. The resulting solution was cooled, diluted with water, and extracted twice with ether. These ether extracts were discarded. The aqueous phase was then acidified to pH 1 with conc HCl and extracted twice with ether. These latter ether extracts were dried (MgSO4), and concentrated to afford 4.47 g of 2-tert-butylbenzoic acid as pure white solid without any further purification, a 96% yield. m.p. 58-60 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3-Amino-6-(2-t-butylbenzyloxy)pyridazine From 2-t-butylbenzyl alcohol to give title compound mp. 147-9 δH(DMSO) 7.4(2H,m,ArH), 7.28(2H,m,ArH), 6.9(1H,JAB,8 Hz,4H), 6.85(1H,JAB,8 Hz,5H), 6.0(2H,brs,NH2), 5.5(2H,s,CH2), 1.4(9H,s,Me3). (Alcohol prepared by LAH reduction of 2-t-butylbenzoic acid; M. Crawford and F. H. C. Stewart, J. Chem. Soc., 1952, 4444). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 163 4-[[(2,6-Dichlorophenyl)carbonyl]amino]-N-[[2-(1,1-dimethylethyl)phenyl]carbonyl]-L-phenylalanine methyl ester was prepared from 4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester and <strong>[1077-58-3]2-(1,1-dimethylethyl)benzoic acid</strong> using the general procedure described in example 3. HR MS: Obs. mass. 527.1523. Calcd. mass. 527.1573 (M+H). |
A390500 [58537-98-7]
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