Water → 5-tert-Butyl4-dimethylthiocarbamoyloxy-2-methyl-benzoic acid methyl ester

To a solution of 5-tert-butyl-4-hydroxy-2-methylbenzoic acid methyl ester from Example BBB (15.1 g, 68 mmol) in DMF (150 mL) was added NaH (3.3 g of a 60% dispersion, 82 mmol), and the mixture was stirred at room temperature for 1 hour. N,N-Dimethylthiocarbamoyl chloride (10.1 g, 82 mmol) was added all at once; the reaction mixture was stirred at 55° C. for 36 hours and then cooled to room temperature. H2O (200 mL) was added, and the solution was extracted with EtOAc. The combined extracts were washed with 1N NaOH, 1N HCl, and brine. The organic phase was dried (MgSO4) and concentrated. The residue was chromatographed on silica gel, eluting with 6:1 hexane:EtOAc, to give the title compound. 1H NMR (CDCl3) δ 1.37 (s, 9 H), 2.55 (s, 3 H), 3.39 (s, 3 H), 3.49 (s, 3 H), 3.89 (s, 3 H), 6.90 (s, 1 H), 8.01 (s, 1 H).

1. stirringthe reaction mixture was stirred at 55° C. for 36 hours
2. temperaturecooled to room temperature
3. extractionthe solution was extracted with EtOAc
4. washThe combined extracts were washed with 1N NaOH, 1N HCl, and brine
5. dry with materialThe organic phase was dried (MgSO4)
6. concentrationconcentrated
7. customThe residue was chromatographed on silica gel
8. washeluting with 6:1 hexane

ORD-Eintrag

ord-d9c08af142a24b23b301b8b6b49be27b

Quelldatensatz

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05834506