Triethylamine → 1-(Chloromethyl)-2,3-bis{[2-(methyloxy)ethyl]oxy}benzene
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:17]O.C(N(CC)CC)C.S(Cl)([Cl:28])=O>ClCCl>[Cl:28][CH2:17][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][CH2:14][O:15][CH3:16])[C:6]=1[O:5][CH2:4][CH2:3][O:2][CH3:1]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (1.12 g, 4.37 mmol) and triethylamine (0.49 g, 4.84 mmol) in dichloromethane (20 mL) was slowly added thionyl chloride (0.78 g, 6.58 mmol) at 0° C. The solution was stirred at 0° C. for 15 min, and then at rt for 3 h. Dichloromethane (80 mL) was added, the solution was washed with water (50 mL), sat. sodium bicarbonate (50 mL), and brine (50 mL), dried with sodium sulfate, and concentrated to give crude 1-(chloromethyl)-2,3-bis{[2-(methyloxy)-ethyl]oxy}benzene (1.15 g, 96% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ7.02 (m, 2H), 6.90 (dd, 1H), 4.72 (s, 2H), 4.27 (m, 2H), 4.14 (m, 2H), 3.77 (m, 2H), 3.73 (m, 2H), 3.46 (s, 3H), 3.44 (s, 3H).
Workup
- customat 0° C
- waitat rt for 3 h
- washthe solution was washed with water (50 mL), sat. sodium bicarbonate (50 mL), and brine (50 mL)
- dry with materialdried with sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cc1deea9b25949c18538cc00c06bfae1
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872014B2
Reaction notes
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