Water → 1-(Chloromethyl)-2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}benzene
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:14]O.N1C=CC=CC=1.S(Cl)([Cl:24])=O.O>O1CCCC1>[Cl:24][CH2:14][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])[C:3]=1[O:2][CH3:1]Participants
6
Procedure
To a solution of (2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)methanol (0.37 g, 1.7 mmol) and pyridine (0.23 mL 2.8 mmol) in tetrahydrofuran (8 mL) at 0° C. was added thionyl chloride (0.14 mL, 1.9 mmol) and the reaction mixture warmed to room temperature and stirred for one hour. Then it was poured into water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined extract was washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give 1-(chloromethyl)-2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}benzene (0.33 g, 1.4 mmol, 82% yield). 1H NMR (400 MHz, CDCl3): 7.01-6.89 (m, 3H), 4.63 (s, 2H), 4.16-4.13 (m, 2H), 3.95 (s, 3H), 3.79-3.77 (m, 2H), 3.44, m, 3H).
Workup
- extractionextracted with ethyl acetate (3×20 mL)
- extractionThe combined extract
- washwas washed with water and brine (20 mL each)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5e3b12a62da943fe874866f78bc39a25
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872014B2
Reaction notes
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