1-Chloro-3-(methoxymethoxy)benzene synthesis
- Product Name:1-Chloro-3-(methoxymethoxy)benzene
- CAS Number:91105-99-6
- Molecular formula:C8H9ClO2
- Molecular Weight:172.61
108-43-0
294 suppliers
$13.00/5g
107-30-2
1 suppliers
$110.00/2.5g
91105-99-6
15 suppliers
$94.00/1g
Yield:91105-99-6 90%
Reaction Conditions:
Stage #1: 3-monochlorophenolwith potassium carbonate in propan-2-one;
Stage #2: chloromethyl methyl ether in propan-2-one at 0 - 25;
Steps:
4 4.2.4. 1-Chloro-3-(methoxymethoxy)benzene (10)25
Potassium carbonate (27.0 g, 195 mmol, 5 equiv) was added to a solution of 3-chlorophenol (5.00 g, 38.9 mmol) in acetone (97 mL, C=0.4 mol/L). The suspension was stirred vigorously and the temperature of the reaction mixture was decreased to 0 °C. Methoxymethyl chloride (MOMCl) (4.44 mL, 58.4 mmol, 1.5 equiv) was added to the reaction mixture. Then, the reaction mixture was allowed to gently reach 25 °C. Water was added (90 mL) and the reaction mixture was diluted with ethyl acetate (90 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (3*90 mL). The combined organic layers were washed with brine (90 mL), dried over Na2SO4, filtered and evaporated to dryness. The crude residue was purified by column chromatography on silica gel (eluent: pentane) to afford 10 as a colorless liquid (6.04 g, 35.0 mmol, 90%). 1H NMR (CDCl3, 300 MHz): δ=7.22 (t, J=8.1 Hz, 1H), 7.08 (t, J=2.1 Hz, 1H), 7.01 (dt, J=8.1, 0.6 Hz, 1H), 6.95 (ddd, J=8.1, 2.1, 0.6 Hz, 1H), 5.18 (s, 2H, CH2), 3.50 (s, 3H, Me) ppm. 13C NMR (CDCl3, 75 MHz): δ=158.0 (CIV, COCH2OMe), 134.8 (CIV, CCl), 130.2, 122.0, 116.8, 114.6, 94.5 (CH2), 56.1 (CH3) ppm.
References:
Augros, David;Yalcouye, Boubacar;Berthelot-Bréhier, Ana?s;Chessé, Matthieu;Choppin, Sabine;Panossian, Armen;Leroux, Frédéric R. [Tetrahedron,2016,vol. 72,# 34,p. 5208 - 5220]
108-43-0
294 suppliers
$13.00/5g
3188-13-4
137 suppliers
$35.00/5G
91105-99-6
15 suppliers
$94.00/1g