Water → (Rac.)-2,6-dichloro-4-(1-hydroxyethyl)phenol

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Reaction Steps

A sol. of 2,6-dichloro-4-hydroxymethylphenol (1.635 g, 8.56 mmol) in Et2O (30 mL) was cooled to −78° C. MeMgBr (3M in Et2O, 7.15 mL, 21.5 mmol) was added dropwise to the cooled reaction mixture over 18 min. Et2O (20 mL) was added again during the addition of MeMgBr. Stirring was continued at −78° C. for 1 h, and then the reaction mixture was allowed to warm up to rt over 1 h. The mixture was cooled to 0° C., and aq. sat. NH4Cl (10 mL) was added dropwise. The mixture was allowed to warm up to rt, and additional aq. sat. NH4Cl (35 mL) and water (35 mL) were added. The phases were then separated and the aq. phase was extracted with Et2O. The combined org. extracts were then washed with brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by FC (EtOAc/heptane, 1:1) yielded the title compound (1.683 g, 95%). LC-MS: tR=0.74 min.

Provenance & Evidence