ChemicalBook CAS DataBase List 1-(3-ACETYL-2,4,6-TRIHYDROXYPHENYL)ETHAN-1-ONE

1-(3-ACETYL-2,4,6-TRIHYDROXYPHENYL)ETHAN-1-ONE synthesis

14synthesis methods

Product Name:1-(3-ACETYL-2,4,6-TRIHYDROXYPHENYL)ETHAN-1-ONE
CAS Number:2161-86-6
Molecular formula:C10H10O5
Molecular Weight:210.18

Preparation by Friedel–Crafts acylation of phloroglucinol,
? with acetic acid,
– by using boron trifluoride-acetic acid complex at
28–30° for 18 h (85%)
with acetic anhydride,
– in the presence of boron trifluoride-ethyl ether complex at 20° for 1 h (80%)
– in the presence of zinc chloride at 145–150° for 15 min (25%);
– in the presence of concentrated sulfuric acid (24%)
? with acetyl chloride,
– (4 equiv.) in the presence of ferric chloride
– in ethyl ether in the presence of aluminium chloride at r.t. for 5 days (8).

108-73-6
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$13.00/5g

75-36-5 Synthesis

75-36-5
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1-(3-ACETYL-2,4,6-TRIHYDROXYPHENYL)ETHAN-1-ONE

2161-86-6
68 suppliers
$25.00/10 mg

Yield:2161-86-6 94%

Reaction Conditions:

with methanesulfonic acid;acetic acid at 80; for 0.5 h;Neat (no solvent);

Steps:

General method for synthesis of diacyl and dimeric phloroglucinols using conventional heating
General Procedure: The mixture of phloroglucinol (1, 1 mmol), acid anhydride/acyl chloride (3 mmol), acetic acid (1 mmol) and methanesulfonic acid (3 mmol) was heated for 30 min at 80 °C. On cooling, water was added and the reaction mixture and was extracted with ethyl acetate. Crude diacyl phloroglucinol derivative were crystallised from methanol. In case of synthesis of dimeric phloroglucinol, after 30 min, the linker aldehyde was added to the reaction mixture and the reaction was continued for further 15 min. After completion of reaction (TLC), water was added to the reaction mixture and extracted with ethyl acetate. Organic layer was dried over sodium sulphate and the solvent was removed under vacuum and the crude product was purified by crystallisation from methanol.

References:

Chauthe, Siddheshwar K.;Bharate, Sandip B.;Periyasamy, Giridharan;Khanna, Amit;Bhutani, Kamlesh K.;Mishra, Prabhu D.;Singh, Inder P. [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 6,p. 2251 - 2256] Location in patent:experimental part

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108-73-6
480 suppliers
$13.00/5g