7150-55-2Relevant academic research and scientific papers
Preparation of cyclopropyl p-hydroxyphenyl ketone and its precursor 3-chloropropyl p-hydroxyphenyl ketone
Chang, Sou-Jen,Fernando, Dilinie P.,King, Steve
, p. 141 - 143 (2013/09/07)
3-Hydroxypropyl p-hydroxyphenyl ketone (7) is selectively prepared in 96% yield by the Friedel-Crafts reaction of anisole, 4-chlorobutyryl chloride (5) and aluminum chloride in chlorobenzene at 100 °C, followed by quenching the mixture in aqueous hydrochloride at 40 °C. Heating of the quenched aqueous mixture to 100 °C converts hydroxyl compound 7 cleanly to 3-chloropropyl p-hydroxyphenyl ketone (2) in 95-99% yield. Compounds 2 and 7 are interchangeable. Heating chloride 2 with aluminum chloride produces alcohol 7; whereas heating 7 in aqueous hydrochloric acid gives 2 exclusively. The chloride 2 is easily converted to cyclopropyl p-hydroxyphenyl ketone (1) at 0 °C using 6 equiv of aqueous sodium hydroxide or 2 equiv of potassium tert-butoxide in 92 and 96% yields, respectively.
A GENERAL ROUTE TO 3-(HYDROXYARYL)TETRAHYDRO PYRIDAZINES AND 1,2-DIAZEPINES AND DERIVATIVES
Kalyanam, N.,Dave, K.G.,Likhate, M.A.
, p. 2183 - 2192 (2007/10/02)
A three step synthesis of 1-acyl-3-(hydroxyaryl)tetrahydro pyridazines and 1,2-diazepines starting from phenols is described.The hydrolytic lability of some intermediate chloroalkyl aryl ketones and a simple recovery of these ketones from nitrobenzene solution are indicated.
