Acetone → HCID 20503926, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethyl terephthalate (10 g, 51.5 mmole) and acetone (4.15 mL, 56.6 mmole) in a mixture of toluene/dimethoxyethane (75 mL/25 mL) was added to a suspension of NaH 60% (2.68 g, 66.9 mmole) in dry toluene (25 mL) under argon. The mixture was heated at 100° C. for 4 hours. The reaction mixture was cooled to rt and 25 mL of water were added. The pH was adjusted to 3-4 with HCl 2N and the mixture was poured into water (300 mL). The aqueous mixture was extracted with ethyl acetate (3×150 mL), dried over sodium sulphate and evaporated to afford a yellow solid which was purified by column cromatography (n-Hex/EtOAc 9:1 to 7:3) to afford the title compound (2.78 g, 25% yield) as a yellow solid.

Provenance & Evidence