p-Toluenesulfonic acid → Carvacrol

Participants

Reaction Conditions

Reaction Steps

A mixture of p-toluenesulfonic acid (1.4 g) and carvone (11.3 g) in chlorobenzene/1,4-dioxane (4:1 by volume; 75 mL) was heated at 180° C. for 35 min, then rapidly cooled using the cold-finger, and extracted with 10% NaOH solution (3×100 mL). The combined aqueous extract was washed with CH2Cl2 (2×100 mL), neutralized by dropwise addition of conc H2SO4, and extracted with CH2Cl2 (3×100 mL). The organic extract was washed with sat NaHCO3 (100 mL), dried with MgSO4, and concentrated in vacuo to give carvacrol (9.6 g; 85%).

Provenance & Evidence