Aluminium lithium hydride → 2,3,6-Trimethyl-4-sulfanylphenol

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Reaction Conditions

Reaction Steps

2,3,5-Trimethyl-4-hydroxyphenylthiocyanate (2 g, 10.35 mmol) was dissolved in 100 mL of anhydrous ether containing 25 mL of anhydrous tetrahydrofuran. This solution was added dropwise over 1 h to 100 mL of anhydrous ether containing LiAlH4 (0.9 g, 24 mmol) at room temperature. After a further hour at 20° C., the unreacted LiAlH4 was destroyed by cooling the heterogeneous mixture to 0° C. and adding moist ether (50 mL), H2O (50 mL), and 1 N HCl (50 mL). A further 50 mL of water was added and the organic phase was separated and washed with water (2×50 mL), NaHCO3 solution (2×50 mL), water (2×50 mL), and saturated NaCl (50 mL). The organic phase was dried over anhydrous MgSO4 and filtered and the solvent removed under reduced pressure. Silica gel column chromatography with 5% ethyl acetate in hexane gave 1.8 g (90%) of 2,3,5-trimethyl-4-hydroxybenzenethiol as a white powder, mp 86° C. [Lit.1 mp 86° C.].

Provenance & Evidence