alpha,alpha'-Dichloro-p-xylene → 1-[4-(Chloromethyl)phenyl]-2,5,8,11,14-pentaoxapentadecane

To a solution of tetraethylene glycol monomethyl ether (2.00 g, 9.61 mmol) in THF (15 mL) at room temperature was added NaH (276.7 mg, 11.53 mmol). The reaction mixture was stirred for 30 min, followed by the addition of 1,4-bis(chloromethyl)benzene (2.01 g, 11.5 mmol). The reaction mixture was stirred at room temperature overnight and subsequently the solvent was evaporated. The reaction mixture was then dissolved in CH2Cl2 and washed with water. The organic phase was dried with Na2SO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography to give the desired compound (2.56 g, 7.40 mmol, 77%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) δ 7.26-7.40 (m, 4H), 4.55 (s, 2H), 4.54 (s, 2H), 3.69−3.56 (m, 14H), 3.53−3.50 (m, 2H), 3.34 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 138.7, 136.8, 128.7, 128.0, 72.8, 71.9, 70.7, 70.6, 70.5, 69.6, 59.1, 46.1; MS (ESI) m/z calculated for C22H35N6O11 [M+H]+ 347.1 found [M+H2O]+ 364.2.

1. stirringThe reaction mixture was stirred at room temperature overnight
2. customsubsequently the solvent was evaporated
3. dissolutionThe reaction mixture was then dissolved in CH2Cl2
4. washwashed with water
5. dry with materialThe organic phase was dried with Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified

ORD record

ord-d5ed2b5708894124922075ef94b2cabf

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08506993B2