ChemicalBook CAS DataBase List 1-(3-CHLORO-4-HYDROXYPHENYL)-1-ETHANONE

1-(3-CHLORO-4-HYDROXYPHENYL)-1-ETHANONE synthesis

9synthesis methods

Product Name:1-(3-CHLORO-4-HYDROXYPHENYL)-1-ETHANONE
CAS Number:2892-29-7
Molecular formula:C8H7ClO2
Molecular Weight:170.59

Preparation by reaction of acetyl chloride on 2-chloro-phenol with aluminium chloride in refluxing carbon disulfide (98%).

4525-75-1
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$34.00/5g

3226-34-4
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2892-29-7
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$21.00/250mg

Yield: 31% ， 23.6 g

Reaction Conditions:

with aluminum (III) chloride in 1,2-dichloro-benzene at 20 - 100; for 5 h;Fries Phenol Ester Rearrangement;

Steps:

5.1.6 2-Hydroxy-3-chloroacetophenone (7)
At room temperature, 6 (152.5 g, 893.7 mmol) was added dropwise to a solution of aluminium chloride (119.0 g, 893.7 mmol) in dichlorobenzene (120 mL). The reaction mixture was stirred at 100 °C for 5 h. After cooling to room temperature, dichloromethane was added and the resulting mixture was poured into H₂SO₄ 2 N at 0 °C. Precipitated 3-chloro-4-hydroxyacetophenone was removed by filtering the mixture. The aqueous layer was separated and extracted with dichloromethane. The organic phases were combined, rinsed with water, dried and concentrated. The residue was crystallized from cyclohexane, yielding additional undesired 3-chloro-4-hydroxyacetophenone (23.6 g) as a yellowish solid and, by concentration of the crystallization mother liquor, 47.3 g (31.0%) of the desired product 7 as a yellow oil: ¹H NMR (CDCl₃) δ 12.84 (br s, 1H, exchangeable with D₂O), 7.67 (dd, 1H), 7.57 (dd, 1H), 6.87 (dd, 1H), 2.66 (s, 3H). 3-Chloro-4-hydroxyacetophenone: m.p. 109 °C; ¹H NMR (CDCl₃) δ 7.98 (d, 1H), 7.81 (m, 1H), 7.08 (m, 1H), 6.30 (br s, 1H, exchangeable with D₂O), 2.56 (s, 3H).

References:

Fumagalli, Laura;Pallavicini, Marco;Budriesi, Roberta;Gobbi, Marco;Straniero, Valentina;Zagami, Michael;Chiodini, Giuseppe;Bolchi, Cristiano;Chiarini, Alberto;Micucci, Matteo;Valoti, Ermanno [European Journal of Medicinal Chemistry,2012,vol. 58,p. 184 - 191]

99-93-4 Synthesis