Hydrochloric Acid → HCID 11839188, compound

Participants

Reaction Conditions

Reaction Steps

Crude 3-phenylsulfanyl-dihydro-furan-2,5-dione (20 g, 91 mmol) was dissolved in CH2Cl2 (30 ml) and cooled to 0° C. Aluminum chloride (18.16 g, 136 mmol) was added and the mixture was stirred at room temperature for 1.5 hr. The reaction mixture was diluted with CH2Cl2 (1000 ml) and poured into ice-cooled conc HCl (1000 ml). The phases were separated and the aqueous phase was extracted with CH2Cl2(×3). The combined organic phases were washed with water, dried (MgSO4) and evaporated to a brown solid. The solid was triturated with Et2O to give 8.98 g of 4-oxo-thiochroman-2-carboxylic acid as a pale brown solid. 1H NMR (DMSO) δ 7.96 (1H, dd), 7.20-7.60 (3H, m), 4.40 (1H, dd), 3.20-3.33 (2H, m).

Provenance & Evidence