toluene-4-sulfonic acid in water; acetone T=0°C; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(i) ZnCl2, (ii) AcOH, (iii) (saponification); Multistep reaction;

n-butyllithium in tetrahydrofuran 1.) -60 deg C to room temperature, 2.) room temperature, 3 h;

1: 97 percent / LAH / diethyl ether / 0 °C 2: 1.) oxalyl chloride, DMSO, 2.) triethylamine / tetrahydrofuran / 1.) -30 deg C, 15 min, 2.) - 60 deg C --> room temperature, room temperature, 1 h 3: 48 percent / nBuLi / tetrahydrofuran / 1.) -60 deg C to room temperature, 2.) room temperature, 3 h View Scheme

1: 1.) oxalyl chloride, DMSO, 2.) triethylamine / tetrahydrofuran / 1.) -30 deg C, 15 min, 2.) - 60 deg C --> room temperature, room temperature, 1 h 2: 48 percent / nBuLi / tetrahydrofuran / 1.) -60 deg C to room temperature, 2.) room temperature, 3 h View Scheme

1: FeCl3 2: NaOAc, aq. AcOH 3: aq. H3PO4 / ethanol View Scheme

1: NaOAc, aq. AcOH 2: aq. H3PO4 / ethanol View Scheme

phosphoric acid in ethanol