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Under a nitrogen atmosphere was prepared a slurry of 21 (25.6 g, 0.174 mol) in a mixture of MeOH (10 ml) and Et2O (12 ml). With cooling, a stream of hydrogen chloride was passed through, giving a solution momentarily followed by a precipitate. The total uptake of HC1 was 15 grams. The reaction mixture was refrigerated for 3 hours, and the solid collected and washed with Et2O to yield 31 grams (82%) of 4-methoxy-3-methylbenzimidate hydrochloride; m.p. 137-140°.

1. temperatureWith cooling
2. customgiving a solution
3. customthe solid collected
4. washwashed with Et2O