Dimethyl Sulfate → 1-Chloro-2-methoxy-4-methylbenzene

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-methylphenol (5.00 g, 35.0 mmol, 1.00 equiv) and potassium carbonate (29.0 g, 2.10 mol, 6 equiv) were combined in DMF and stirred 15 minutes. Dimethyl sulfate (9.95 mL, 1.05 mol, 3.00 equiv) was added and the mixture was heated to 70° C. After 1 hour, the reaction was cooled to room temperature and stirred an additional 18 hours. The mixture was diluted with 200 mL H2O and extracted with Et2O. The organic phase was washed three times with H2O and once with brine, then dried over MgSO4 and concentrated en vacuo. 5.48 g (100%) of the product was obtained as a red liquid. 1H NMR (400 MHz, CDCl3) 7.25 (d, 1H), 6.77 (s, 1H), 6.73 (d, 1H), 3.91 (s, 3H), 2.56 (s, 3H).

Provenance & Evidence