Hydrochloric Acid → 2-Nitro-5-(3-phenoxypropoxy)-indan-1,3-dione

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-(3-phenoxypropoxy)-indan-1,3-dione (0.296 gm, 0.001 mole) was suspended in dry ether (10 ml) and cooled to 0° C. The stirred mixture was treated with fuming nitric acid (1 ml) added dropwise over 15 mins and stirred in the ice bath for 1 hr. The mixture was then stirred at r.t. for a further 11/2 hrs. During this time all the solid dissolved leaving a deep yellow solution. Dilute hydrochloric acid (20 ml) was added and the ether evaporated in vacuo. A yellow gum formed which solidfied on scratching to give 0.25 gm of yellow solid which had mp 77°-79° C.(d). (73%). (Found; C, 60.71; H, 4.58; N, 3.66; C18H15NO6.0.75H2O requires; C, 60.92; H, 4.69; N, 3.95%).

Provenance & Evidence