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

Temperature

0 °C

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.].

1. waitAfter a further hour at 20° C.
2. customthe unreacted LiAlH4 was destroyed
3. additionadding moist ether (50 mL), H2O (50 mL), and 1 N HCl (50 mL)
4. additionA further 50 mL of water was added
5. customthe organic phase was separated
6. washwashed with water (2×50 mL), NaHCO3 solution (2×50 mL), water (2×50 mL), and saturated NaCl (50 mL)
7. dry with materialThe organic phase was dried over anhydrous MgSO4
8. filtrationfiltered
9. customthe solvent removed under reduced pressure

ORD record

ord-28918b46f3f742da9115d1e0e7e83fc1

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06703384B2