Water → Tyrosol

Participants

Reaction Steps

A solution of BH3.(CH3)2S (500 mL, 2M in tetrahydrofuran) was added dropwise to a solution of methyl 4-hydroxyphenylacetate (116 g, 0.70 mole) in 300 mL dry tetrahydrofuran. This solution was heated at reflux for 2 hr and stirred at room temperature for 12 hr. TLC indicated the presence of phenol and another 30 mL of BH3.(CH3)2S solution was added. This solution was refluxed for 1 hr, cooled, and then hydrolyzed by dropwise addition of water. The mixture was concentrated in vacuo and the residue triturated with ethyl ether. The ethyl ether portion was dried (MgSO4) and concentrated in vacuo to give 90 g (93%) of 4-(2-hydroxyethyl)phenol, m.p. 84°-86°.

Provenance & Evidence