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CAS No. : | 26191-64-0 | MDL No. : | MFCD00218802 |
Formula : | C13H12O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 184.23 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
beim Belichten.Irradiation; | ||
Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 2: 77 percent / NaBr / Co-Mn-ZrO / acetic acid; acetic anhydride / 105 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | 4'-Methyl-biphenyl-4-ol (Intermediate 5; 2.0 g, 10.9 mmol) was added to a suspension of sodium hydride (60% dispersion; 384 mg, 9.6 mmol) in N,N-dimethylformamide (30 mL) and the mixture was stirred at -5 C. for 20 min. A solution of 5-(chloro-methyl)-furan-2-carboxylic acid ethyl ester (1.6 g, 8.5 mmol) in N,N-dimethylformamide (60 mL) was added and the reaction mixture was stirred overnight at room temperature. The solvents were evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate, and the combined organic layers were washed with water and brine, dried (sodium sulfate), filtered, evaporated, and chromatographed, eluting with 0-50% methylene chloride/hexanes to give 5-(4'-methyl-biphenyl-4-yloxymethyl)-furan-2-carboxylic acid ethyl ester (2.4 g, 84%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 100℃; for 16h; | Method 6C: using the appropriate hydroxyphenylboronic acid. The Suzuki reaction was followed by O-alkylation. The aromatic methyl was then free-radical brominated.Suzuki ReactionTo a solution of bromotoluene (1eq) in dioxane (30eq) were added the appropriate hydroxyphenylboronic acid (1.1eq), the tetrakis(triphenylphosphine)palladium (Pd[P(Ph)3]4) derivative (0.03eq) and potassium carbonate (3eq). The reaction mixture was stirred at 100° C. for 16 hours. After cooling down, the solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed over silica gel.6.6.1 4'-methylbiphenyl-4-ol Prepared following the Suzuki reaction previously described (Method 6C) using 4-bromotoluene and 4-hydroxyphenylboronic acid. The product was chromatographed over silica gel (eluent cyclohexane/ethyl acetate 9/1). The product was obtained as a pale yellow solid. Yield: 49percent Rf (cyclohexane/ethyl acetate 8/2): 0.37 NMR 1H (CDCl3): 2.44 (s, 3H); 4.83 (s, 1H); 6.94 (d, 2H, J=8 Hz); 7.30 (d, 2H J=8 Hz); 7.50 (t, 4H, J=8 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With calcium hydroxide In neat (no solvent) at 80℃; for 2.6h; Sealed tube; | General Methylation Procedure B (Neat Conditions) General procedure: A 10-mL glass reaction tube fitted with a resealable Teflon valve wascharged with the heteroatom nucleophile substrate (1.0 mmol, 1.0equiv), Ca(OH)2 (100 mg, 1.35 mmol, 1.35 equiv), and TMP (0.20 mL,1.7 mmol, 1.7 equiv). The flask was sealed and heated at 80 °C withoutstirring until TLC indicated complete conversion. The reactionwas then worked up as described below. Workup Procedure AAfter complete conversion, 1 N HCl (5 mL) was added and the mixturewas extracted with CH2Cl2 (10 mL). The organic phase was separated,washed with H2O (20 mL), dried over Na2SO4, filtered, and then concentratedin vacuo. The resulting residue was purified by silica gelcolumn chromatography to afford the desired methylated product.Workup Procedure BAfter complete conversion, petroleum ether (5 mL) was added, andthe solid was smashed into fine particles using a spatula and sonicatedfor 5 min. The resulting residue was then directly subjected to silicagel column chromatography to afford the desired methylated product.Workup Procedure CAfter complete conversion, CH2Cl2 (5 mL) was added, and the mixturewas filtered through a pad of Celite, washed with H2O (10 mL), andextracted with EtOAc (5 × 20 mL). The organic phase was separated,dried over Na2SO4, filtered, and concentrated in vacuo. The resultingresidue was purified by silica gel column chromatography to affordthe desired methylated product. |