Potassium Hydroxide → 4,9-Dihydro-s-indaceno[1,2-b:5,6-b']dithiophene

Participants

Reaction Conditions

Reaction Steps

Hydrazine hydrate (11.9 cm3, 245 mmol) is added to a suspension of 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene-4,9-dione (9.6 g, 32.6 mmol) and KOH (5.5 g, 97.8 mmol) in diethylene glycol (100 cm3). The mixture is heated to 180° C. for 6 hours, and then allowed to cool to 23° C. overnight. NH3/H2O (1:1, 200 cm3) is added and the mixture is stirred for 30 minutes. The solid is collected by filtration, washed with H2O (2×300 cm3) and IMS (2×300 cm3), and dried under vacuum to yield the product as a brown solid (6.89 g, 79%). 1H NMR (300 MHz, d6-DMSO): δ(ppm) 7.71 (s, 2H, Ar—H), 7.55 (d, J=4.9 Hz, 2H), 7.21 (d, J=4.9 Hz, 2H, Ar—H), 3.77 (s, 4H, CH2).

Provenance & Evidence