DIETHYL TEREPHTHALOYLDIACETATE synthesis
- Product Name:DIETHYL TEREPHTHALOYLDIACETATE
- CAS Number:93-94-7
- Molecular formula:C16H18O6
- Molecular Weight:306.31
Yield:93-94-7 50%
Reaction Conditions:
with sodium hydride in N,N-dimethyl-formamide at 0 - 20; for 72 h;Inert atmosphere;
Steps:
Ethyl 3-(4-(3-ethoxy-3-oxo-propanoyl)phenyl)-3-oxo-propanoate 17
To a solution of 1,4-diacetylbenzene (500 mg, 3.08 mmol) in anhydrous DMF (15 mL) underargon at 0 °C was added sodium hydride (60%; 493 mg, 12.3 mmol), and the mixture allowed towarm to ambient temperature and stirred for 10 min. Diethyl carbonate (1.49 mL, 12.3 mmol)was added and the reaction mixture stirred at ambient temperature for 3 days. Water (50 mL) wasadded and the mixture extracted with ethyl acetate (3 × 25 mL). The combined organic extractswere washed with saturated brine (50 mL), dried (MgSO4) and concentrated under reducedpressure. Purification by column chromatography, eluting with light petroleum-ethyl acetate(4:1), gave a 1:0.4 mixture of the title compound and mono-enolized tautomer as a colourlesssolid (469 mg, 50%); mp 70-71 °C (lit.,8 mp 72-74 °C); (Found: M+Na+, 329.0992. C16H18NaO6+requires 329.0996); νmax (CHCl3)/cm-1 2986, 1738, 1689, 1623, 1566, 1509, 1468, 1384, 1264,1192, 1033; δH (400 MHz; DMSO-d6) 12.56 (0.4 H, br s, OH), 8.10 (4 H, s, ArH), 8.04 (1.6 H, s,ArH), 6.11 (0.4 H, s, C=CH), 4.28 (4.8 H, s, CH2), 4.26-4.24 (0.8 H, m, OCH2CH3), 4.13 (4.8 H,q, J 7.0, OCH2CH3), 1.20 (1.2 H, t, J 7.0, OCH2CH3), 1.19 (7.2 H, t, J 7.0, OCH2CH3); δC (100MHz; DMSO-d6) bis-β-ketoester: 193.4 (C), 167.5 (C), 139.2 (C), 128.8 (CH), 60.7 (CH2), 45.8(CH2), 13.97 (Me); δC (100 MHz; DMSO-d6) mono-enolized tautomer: 193.4 (C), 193.1 (C),172.4 (C), 167.5 (C), 139.2 (C), 137.7 (C), 128.8 (CH), 126.4 (CH), 89.8 (CH), 60.5 (CH2), 45.8(CH2), 45.7 (CH2), 14.08 (Me), 13.97 (Me); m/z (ESI) 329 (M+Na+, 100%).
References:
Patel, Alpa;Lewis, William;Searle, Mark S.;Stevens, Malcolm F.G.;Moody, Christopher J. [Tetrahedron,2015,vol. 71,# 39,art. no. 26687,p. 7339 - 7343] Location in patent:supporting information
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