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CAS No. : | 81172-89-6 | MDL No. : | MFCD00010217 |
Formula : | C12H16O3 | Boiling Point : | No data available |
Linear Structure Formula : | (OHC)C6H4(CH(OC2H5)2) | InChI Key : | HTMXMFARWHNJDW-UHFFFAOYSA-N |
M.W : | 208.25 | Pubchem ID : | 595993 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
2197 g | A solution of <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (1.13 kg, 8.21 mol) in MeOH (14.3 L) is stirred at about 20 °C. then Et3N (1.06 kg, 1.43 L, 8.21 mol) is added. The mixture is stirred for at least 5 min then terephthalaldehyde diethyl acetal (1.43 kg, 6.84 mol) is added while maintaining the reaction temperature between 20-25 °C. The mixture is stirred for at least 45 min to form the imine. NaBH4 caplets (414 g, 11.0 mol) are added while maintaining the reaction temperature below about 25 °C. The mixture is stirred for 1 h after the addition is completed. The reaction mixture is quenched by adding 1 M NaOH (13.7 L) then extracted with MTBE. The organic solution was washed with brine (7.13 L) then dried (Na2S04) and concentrated to afford Compound A-2 (2197 g; 109percent yield, 94.4 area percent purity by HPLC) as a hazy oil. ? NMR (400 MHz, CDC13) ? 7.43 (d, J= 8.1 Hz, 2H), 7.31 (d, J = 8.1 Hz, 2H), 5.49 (s, 1H), 4.66 (br s, 1H), 4.03 - 3.91 (m, 2H), 3.82 (s, 2H), 3.69 - 3.47 (m, 4H), 3.38 (td, J= 1 1.6, 2.1 Hz, 2H), 2.78 - 2.65 (m, 1H), 1.90 - 1.81 (m, 2H), 1.53 - 1.37 (m, 2H), 1.23 (t, J= 7.1 Hz, 6H). | |
2197 g | A solution of <strong>[33024-60-1]tetrahydro-2H-pyran-4-amine hydrochloride</strong> (1.13 kg, 8.21 mol) in MeOH (14.3 L) is stirred at about 20 °C. then Et3N (1.06 kg, 1.43 L, 8.21 mol) is added. The mixture is stirred for at least 5 min then terephthalaldehyde diethyl acetal (1.43 kg, 6.84 mol) is added while maintaining the reaction temperature between 20-25 °C. The mixture is stirred for at least 45 min to form the imine. NaBH4 caplets (414 g, 11.0 mol) are added while maintaining the reaction temperature below about 25 °C. The mixture is stirred for 1 h after the addition is completed. The reaction mixture is quenched by adding 1 M NaOH (13.7 L) then extracted with MTBE. The organic solution was washed with brine (7.13 L) then dried (Na2S04) and concentrated to afford Compound A-2 (2197 g; 109percent yield, 94.4 area percent purity by HPLC) as a hazy oil. ? NMR (400 MHz, CDC13) ? 7.43 (d, J= 8.1 Hz, 2H), 7.31 (d, J = 8.1 Hz, 2H), 5.49 (s, 1H), 4.66 (br s, 1H), 4.03 - 3.91 (m, 2H), 3.82 (s, 2H), 3.69 - 3.47 (m, 4H), 3.38 (td, J= 1 1.6, 2.1 Hz, 2H), 2.78 - 2.65 (m, 1H), 1.90 - 1.81 (m, 2H), 1.53 - 1.37 (m, 2H), 1.23 (t, J= 7.1 Hz, 6H). |
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