METHYL 3,5-BIS(2-PROPYNYLOXY)BENZENECARBOXYLATE synthesis
- Product Name:METHYL 3,5-BIS(2-PROPYNYLOXY)BENZENECARBOXYLATE
- CAS Number:768387-51-5
- Molecular formula:C14H12O4
- Molecular Weight:244.24
Yield:768387-51-5 99%
Reaction Conditions:
Stage #1: 1-carbomethoxy-3,5-dihydroxybenzenewith 18-crown-6 ether;potassium carbonate in tetrahydrofuran at 20; for 1 h;Inert atmosphere;
Stage #2: propargyl bromide in tetrahydrofuran at 65; for 16 h;Inert atmosphere;Enzymatic reaction;
Steps:
2.2d Synthesis of 1g
To a 500 mL RB flask containing K2CO3 (82.194 g, 594.707 mmol), methyl-3,5-dihydroxybenzoate (1f, 10 g, 59.47 mmol) dissolved inTHF (250 mL) was added under nitrogen atmosphere. Subsequently,18-crown-6 ether was added and the resulting mixture was stirred for 1 h at room temperature. Propargyl bromide (53.06 mL, 356.82 mmol)was added and the reaction mixture was heated to reflux for 16 h. The crudewas extracted with DCM, the separated organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Thecrude product purified through silica column chromatography using 9% ethyl acetate in petroleum ether as eluent to afford the desired product 1g as a colorless solid (99%).M.p. = 111 °C. 1H NMR (500 MHz, CDCl3), δ (ppm) =7.330-7.325 (d, J = 2.3 Hz, 2H), 6.84 (t, J = 2.3 Hz, 1H),4.746 (d, J = 2.40 Hz, 4H), 3.941 (s, 3H), 2.572 (t, J =2.40 Hz, 2H);13C NMR (125 MHz, CDCl3), δ (ppm) =165.43, 157.50, 131.14, 107.89, 106.51, 74.96, 55.11,51.33.GC-MS (EI)-m/z for C14H12O4: 244.07 (calcd.); 244(expt.).
References:
Krishnan, Nithiyanandan;Ameena, M A Hanna;Atchimnaidu, Siriki;Perumal, Devanathan;Golla, Murali;Krishna, Jithu;Varghese, Reji [Journal of Chemical Sciences,2018,vol. 130,# 10,art. no. 141]
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