4-Hydroxybenzyl Alcohol → HCID 18964645, compound

Participants

Reaction Steps

In a 500 mL three-neck round-bottom flask equipped with an overhead stirrer and a reflux condenser were placed 21.7 g of 4-hydroxybenzyl alcohol, and 65 mL of dimethyl sulfoxide. To this solution was slowly added 6.99 g of NaOH, while keeping the temperature below 45° C. After the solution was completed, 20.4 mL of 2-chloroethyl vinyl ether was added slowly while keeping the temperature at 60° C. The reaction mixture was heated at this temperature for 2 hours, and the progress of the reaction was followed by GC. After cooling, the reaction product was added dropwise to 500 mL of water. The precipitated product was then filtered and redissolved in 500 mL of diethyl ether. The ether layer was washed one time with 100 mL of 3% aqueous NaOH and two times with 100 mL portions of distilled water. The ether layer was dried with sodium sulfate, filtered and evaporated. A 55% yield of 2-(4-hydroxymethyl-phenoxy)ethyl vinyl ether was obtained.

Provenance & Evidence