1: (i) pentyl nitrite, aq. HCl, AcOH, (ii) Py 2: aq. H2SO4 / Heating 3: (i) KOtBu, (ii) aq. HCl, AcOH, (heating), (iii) (decarboxylation) 4: KOH, N2H4*H2O / bis-(2-hydroxy-ethyl) ether / Heating 5: HF 6: (i) KOH, N2H4*H2O, (heating), (ii) Pd-C, (heating) View Scheme

sulfur; xylene

1: chloranil; xylene 2: KMnO4 3: polyphosphoric acid 4: N2H4+H2O; NaOH View Scheme