Hydrochloric Acid → HCID 9903861, compound

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Reaction Steps

Dimethylthiocarbamic acid S-(2-tert-butyl-4-formyl-5-methylphenyl) ester (4a) (6.0 gm, 21 mmol) was dissolved in THF and treated with lithium borohydride (0.8 gm) in portions. The mixture was cooled in an ice bath and stirring continued for 1.5 hours. Toluene (25 mL) and water (10 mL) were added followed by cautious addition of 37% hydrochloric acid (2.8 gm) to destroy excess borohydride and adjust the pH to 6.5. The aqueous layer was separated and the organic layer extracted with 1 N NaOH (2×10 mL) and water (10 mL) and concentrated to a solid. This was recrystallized from toluene and heptane and the crystals vacuum dried at 40° C. to give dimethylthiocarbamic acid S-(2-tert-butyl-4-hydroxymethyl-5-methylphenyl) ester (5a) (5.6 gm): mp: 135.9-136.4° C.; HPLC: 99.1%.

Provenance & Evidence