Benzoic Acid, 3,5-Diethoxy-, Methyl Ester synthesis
- Product Name:Benzoic Acid, 3,5-Diethoxy-, Methyl Ester
- CAS Number:198623-55-1
- Molecular formula:C12H16O4
- Molecular Weight:224.25
2150-44-9
269 suppliers
$5.00/5g
75-03-6
364 suppliers
$11.00/5g
198623-55-1
27 suppliers
$110.00/50mg
Yield:198623-55-1 82 %
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 70;Inert atmosphere;
Steps:
methyl 3,5-diethoxybenzoate (3m,m')
To a suspension of K2CO3 (1.360 g, 9.81 mmol) and methyl 3,5-dihydroxybenzoate 2m,m' (550 mg, 3.27 mmol) in DMF (2.5 mL), EtI (1.530 g, 0.79 mL, 9.81 mmol) was added. The suspension was stirred at reflux overnight, then the system was diluted with CHCl3 (6 mL). Water (10 mL) was added and extracted with CHCl3 (3 10 mL). The combined organic extracts were washed with brine (3 5 mL), dried over MgSO4, filtered and the solvents removed under reduced pressure. The crude was purified by silica gel chromatography (cyclohexane/EtOAc 5:5) to give pure 3m,m' as a white solid (602 mg, 82% yield). Spectral properties are in agreement with those reported in the literature.11 1H NMR (400 MHz, CDCl3) δ 7.16 - 7.12 (bs, 2H, Hb), 6.70 - 6.59 (bs, 1H, He), 4.05 (q, JH,H = 7.0 Hz, 4H, Hc), 3.89 (s, 3H, Ha), 1.41 (t, JH,H = 7.0 Hz, 6H, Hd); 13C NMR (100 MHz, CDCl3) δ 167.1, 160.1, 132.0, 107.8, 106.8, 63.9, 52.3, 14.9; LRMS (ESI): m/z calcd for C12H16O4+Na+: 247.09 [M+Na]+; found: 247.09.
References:
Romito, Deborah;Amendolare, Leonardo;Kalathil, Krishnan K.;Bonifazi, Davide [Synthesis,2023,vol. 55,# 2,p. 359 - 367] Location in patent:supporting information
74-96-4
450 suppliers
$9.00/5g
2150-44-9
269 suppliers
$5.00/5g
116169-07-4
15 suppliers
inquiry
198623-55-1
27 suppliers
$110.00/50mg
116169-07-4
15 suppliers
inquiry
75-03-6
364 suppliers
$11.00/5g
198623-55-1
27 suppliers
$110.00/50mg
124480-95-1
61 suppliers
$60.00/100mg
18107-18-1
210 suppliers
$33.00/5g
198623-55-1
27 suppliers
$110.00/50mg