反应详情

To a solution of 3-chloro-4-(hydroxymethyl)phenol (for a preparation see Intermediate 16)(3 g, 18.9 mmol) in ethanol (80 ml) was added benzyl bromide (2.25 ml, 18.9 mmol, Aldrich) and then 2 M aqueous sodium hydroxide (10.4 ml, 20.8 mmol). The mixture was stirred at ambient temperature overnight under nitrogen. The solvent was removed in vacuo to leave an aqueous suspension. The residue was partitioned between dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase extracted with dichloromethane (50 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to leave an oil. The residue was loaded in dichloromethane and purified on silica (100 g×2) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give {2-chloro-4-[(phenylmethyl)oxy]phenyl}methanol as a white solid (2.18 g).

1. customThe solvent was removed in vacuo
2. customto leave an aqueous suspension
3. customThe residue was partitioned between dichloromethane (100 ml) and water (100 ml)
4. customThe phases were separated
5. extractionthe aqueous phase extracted with dichloromethane (50 ml)
6. dry with materialThe combined organic extracts were dried (MgSO4)
7. filtrationfiltered
8. customthe solvent removed in vacuo
9. customto leave an oil
10. custompurified on silica (100 g×2)
11. customevaporated in vacuo