Sulfuric Acid → HCID 15045078, compound

Participants

Reaction Steps

A solution of 2-[(4-methylfluoren-9-yl)ethyl]-1,3-dioxolane (11.1 g, 39.6 mmol) in acetone (150 mL) at 0° C. was charged with Jone's reagent (16 g of CrO3 and I6 ml of H2SO4 (conc.) in 100 ml of water). The reaction mixture was stirred overnight at room temperature. The reaction was monitored by TLC (silica, 25% EtOAc in hexane). The acetone was evaporated, the residue was diluted with water (100 mL). The product was extracted into EtOAc and the organic layer was washed thoroughly with water (×6), until aqueous washings were clear, then the product was extracted into 1N NaOH solution (3×70 mL), the water was washed again with ethyl acetate (1×30 mL) and acidified to pH=1. The solid formed was filtered off, washed with water and dried. This afforded 6.8 g (68.2%) of the 3-(4-methylfluoren-9-yl)propionic acid.

Provenance & Evidence