4-hydroxy-4'-methylbenzophenone synthesis

10synthesis methods

Product Name:4-hydroxy-4'-methylbenzophenone
CAS Number:134-92-9
Molecular formula:C14H12O2
Molecular Weight:212.24

Preparation by reaction of p-methylbenzoyl chloride with phenol in the presence of aluminium chloride.

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Yield: 94%

Reaction Conditions:

with aluminum (III) chloride in toluene at 130; for 2 h;Inert atmosphere;

Steps:

1.4. General method for demethylation of 3b, 3d-l and 3n-p with aluminum trichloride (4b, 4d-l and 4n-p).[10]
General procedure: AlCl3 (2.5 equiv.) was slowly added to a solution of 3b, 3d-l and 3n-p (1.0 equiv.) in toluene (0.15 M) under a N2 atmosphere. The mixture was refluxed at 130 °C for 2 h and by TLC (Pet. ether/EtOAc 4/1) full conversion was shown. The cooled mixture was poured into an 3 M HCl (aq.) solution, the organics were extracted with ethyl acetate (3 times), washed with brine, dried over MgSO4 and concentrated to give the desired 4-(benzoyl)phenols (4b, 4d-l and 4n-p) as solids.

References:

Yu, Zhiyi;Van Veldhoven, Jacobus P.D.;'T Hart, Ingrid M.E.;Kopf, Adrian H.;Heitman, Laura H.;Ijzerman, Adriaan P. [European Journal of Medicinal Chemistry,2015,vol. 106,p. 50 - 59] Location in patent:supporting information

201230-82-2 Synthesis