Triethylamine → 1-(Chloromethyl)-4-methoxy-2-methylbenzene
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]O)=[C:5]([CH3:11])[CH:4]=1.C(N(CC)CC)C.CS([Cl:23])(=O)=O>C1(C)C=CC=CC=1>[Cl:23][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (4-methoxy-2-methylphenyl)methanol (8.2 g, 54.0 mmol) and triethylamine (9.1 mL, 65.0 mmol) in toluene (100 mL) at 0° C., methanesulfonyl chloride (5.1 mL, 65.0 mmol) was added via syringe over 20 min. The ice water bath was removed, and the reaction was allowed to stir at room temperature for 30 min, heated at 80° C. for 3 days, and then concentrated. The reaction was diluted with DCM, washed with H2O (3×100 mL) and brine, dried over Na2SO4, and concentrated under reduced pressure to 1-(chloromethyl)-4-methoxy-2-methylbenzene (8.1 g) as a dark brown oil. 1H NMR (300 MHz, CDCl3): δ 7.25 (d, 1H), 6.75 (m, 2H), 4.62 (s, 2H), 3.82 (s, 3H), 2.43 (s, 3H).
Workup
- customThe ice water bath was removed
- temperatureheated at 80° C. for 3 days
- concentrationconcentrated
- additionThe reaction was diluted with DCM
- washwashed with H2O (3×100 mL) and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure to 1-(chloromethyl)-4-methoxy-2-methylbenzene (8.1 g) as a dark brown oil
Sources & evidence
- ORD record
- ord-fcf26b0863fe4a148067ba730665034b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09078871B2
Reaction notes
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