ChemicalBook CAS DataBase List 4'-Hydroxypropiophenone

4'-Hydroxypropiophenone synthesis

10synthesis methods

Product Name:4'-Hydroxypropiophenone
CAS Number:70-70-2
Molecular formula:C9H10O2
Molecular Weight:150.17

Preparation by Fries rearrangement of phenyl propionate
with aluminium chloride in refluxing carbon disulfide ? then at 130–150° for 2–3 h after solvent elimination (45–50%)
with aluminium chloride in nitrobenzene at 50° for 18 h (72%) or at ? 20° for 48 h (60%)
with aluminium chloride in nitromethane at 20° for 7–8 days (80%)
with aluminium chloride in chlorobenzene using microwave irradiation for ? 3 min at 106° (62%)
with aluminium chloride in ethylene dichloride at 95° for 5 h or in heptane at ? 80–90° for 7 h (36%), in benzene or in tetrachloroethane at 80°; with aluminium chloride in the presence of propionyl chloride at 50–60° for ? 6 h (49%)
with aluminium chloride without solvent at 50° for 10 h
with titanium tetrachloride in nitromethane at 20° for 7 days (56%) or ? without solvent at 50° for 10 h (39%)
with polyphosphoric acid at 100° (61%)
with boron trifluoride at 50° for 3 h (46%)
with stannic chloride at 50° for 3 h (10%).

79-03-8 Synthesis

79-03-8
407 suppliers
$9.00/1g

108-95-2 Synthesis

108-95-2
737 suppliers
$14.00/25g

70-70-2
475 suppliers
$13.00/25g

Yield:70-70-2 99%

Reaction Conditions:

with trifluorormethanesulfonic acid at 0 - 20; for 1 h;regiospecific reaction;Friedel-Crafts acylation;

Steps:

4.3. General procedure of Friedel-Crafts acylation of phenols in TfOH

General procedure: Phenol (0.28 mmol) and acyl chloride (0.28 mmol) were dissolved in TfOH (3 ml) at 0 °C. The reaction mixture was warmed to room temperature for appropriate time in Table 2, then poured into cold water and ethyl acetate. The organic layer was washed with 1 M HCl, saturated NaHCO₃, and saturated NaCl, and dried over MgSO₄, then filtrated. The filtrate was concentrated and the residue was subjected silica column chromatography to afford acylated products. All spectral data were identical with the literatures.²⁷

References:

Murashige, Ryo;Hayashi, Yuka;Ohmori, Syo;Torii, Ayuko;Aizu, Yoko;Muto, Yasuyuki;Murai, Yuta;Oda, Yuji;Hashimoto, Makoto [Tetrahedron,2011,vol. 67,# 3,p. 641 - 649] Location in patent:experimental part

802294-64-0 Synthesis