ChemicalBook CAS DataBase List 3,5-DIMETHYL-4-HYDROXYACETOPHENONE

3,5-DIMETHYL-4-HYDROXYACETOPHENONE synthesis

9synthesis methods

Product Name:3,5-DIMETHYL-4-HYDROXYACETOPHENONE
CAS Number:5325-04-2
Molecular formula:C10H12O2
Molecular Weight:164.2

Preparation by Fries rearrangement of 2,6-dimethylphenyl acetate, ? with aluminium chloride, without solvent at 120–140°,in nitrobenzene at r.t. (75%) or in nitromethane, first at 0°, then at 50° for 48 h under argon atmosphere (61%)
with aluminium bromide without solvent at 130° (71%).

576-26-1 Synthesis

576-26-1
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$10.00/25g

75-36-5 Synthesis

75-36-5
579 suppliers
$17.92/100G

5325-04-2
55 suppliers
$50.00/2 g

Yield:-

Reaction Conditions:

aluminium trichloride in dichloromethane

Steps:

6.1 EXAMPLE 6
(1) Synthesis of 2,6-dimethyl-4-acetylphenol. To an ice-cooled solution of 2,6-dimethylphenol (12.2 g, 0.1 mmol) in dichloromethane, anhydrous aluminum chloride (14.4 g) was slowly added with stirring, followed by slow addition of acetyl chloride (9.4 g). The reaction mixture was stirred at 10° C. or below for 1 h, then at room temperature for 3 h. Thereafter, the mixture was poured into ice water. Then, the reaction product was extracted with dichloromethane and the extracted layer was washed with water. Further, the extracted layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized with benzene, giving the desired compound, 2,6-dimethyl-4-acetylphenol in an amount of 1.9 g. ¹ H-NMR: δ2.25(6H, s), 2.51 (3H, s), 5.7 (1H, br), 7.51 (2H, s) MS: M⁺ 164

References:

Mochida Pharmaceutical Co., Ltd. US5438139, 1995, A