Hydroquinone → HCID 70363015, compound

Participants

Reaction Steps

A magnetically-stirred solution of 3,5,6,7-tetrahydro-1H-thieno[3,4-b]pyran-5-one (14.32 g, 0.09168 mol) in benzene (150 mL) was treated, in portions, with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (21.29 g, 0.09378 mol). The DDQ dissolved exothermically, giving a dark brown solution which gradually faded to orange, as the crystalline hydroquinone separated. The solids were removed by filtration and rinsed with CH2Cl2. The filtrates were concentrated in vacuo, and the residue was twice distilled (Kugelrohr) to give a mobile light orange oil. (bp>141° C./1.8 Torr or 126°-145° C./0.55 Torr, external temperature). Yield: 11.98 g (84.7%). The product solidified upon storage under N2 at -20° C. NMR and GC/MS data were in agreement with the proposed structure. The compound is sensitive to water, oxygen and light.

Provenance & Evidence