ChemicalBook CAS DataBase List 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE

2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE synthesis

6synthesis methods

Product Name:2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE
CAS Number:1641-17-4
Molecular formula:C15H14O3
Molecular Weight:242.27

Preparation by Friedel–Crafts acylation of m-methoxy-phenol with p-toluoyl chloride,
in the presence of boron trichloride in benzene first at ?10°, then at reflux for 10 h under nitrogen (80%)
in the presence of titanium tetrachloride in benzene first at ?10°, then at reflux for 14 h under nitrogen (73%) or in chlorobenzene for 1 h at 120° (79%).

874-60-2 Synthesis

874-60-2
420 suppliers
$10.00/5g

151-10-0
471 suppliers
$5.00/10g

2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE

1641-17-4
97 suppliers
$70.00/100mg

Yield:1641-17-4 51%

Reaction Conditions:

with aluminum (III) chloride in dichloromethane at 0 - 20;chemoselective reaction;Friedel-Crafts Acylation;

Steps:

Friedel-Crafts Reactions of Aryl Methyl Ethers 8, 10-12 with Acyl Chlorides 6, 7, and 13; General Procedure A

General procedure: AlCl3 (467 mg, 3.5 mmol) was suspended in CH2Cl2 (10 mL) in a round-bottom flask. The corresponding aryl methyl ether 8 or 10-12 (1.0 mmol) was added to this suspension and the mixture was cooled down to 0 °C. After stirring for 5 min, the corresponding acyl chloride 6, 7, or 13 (1.5 mmol) was added dropwise and the resulting mixture was stirred at r.t. The progress of the reaction was monitored by TLC (hexane/EtOAc, 8:2). At the end of the reaction (5-10 h), the mixture was poured into aq 1 N HCl and extracted with CH2Cl2 (4 ×). The combined organic phases were washed with aq 1 N HCl, aq NaHCO3 (with the exception of reactions with 7) and H2O, and dried over MgSO4. The solvents were evaporated under reduced pressure and the remaining residue was purified by column chromatography.

References:

Richter, Celin;Ernsting, Nikolaus P.;Mahrwald, Rainer [Synthesis,2016,vol. 48,# 8,p. 1217 - 1225]