Phthalic Anhydride → cis-1,2-Dihydroxymethylcyclohex-4-ene

Participants

Reaction Conditions

Reaction Steps

To a 0° C. suspension of lithium aluminum hydride (4 eq) in dry THF (250 mL) was added portionwise phtalic anhydride over 20 minutes. The mixture was brought to room temperature then warmed to reflux for 6 hours then cooled to 0° C. The reaction was quenched with saturated sodium sulfate solution, filtered and concentrated. The residue was taken into ethyl acetate washed with water, brine, dried and concentrated to yield the desired compound as a viscous oil. 1HNMR (500 mHz, CDCl3): 5.62 ppm (s, 2H); 3.76-3.70 (m, 2H); 3.72-3.55 (m, 4H), 2.20-1.98 (m, 6H).

Provenance & Evidence