2′-Hydroxy-5′-methoxyacetophenone
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2′-Hydroxy-5′-methoxyacetophenone
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CAS No:
705-15-7
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Formula:
C9H10O3
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Chemical Name:
2′-Hydroxy-5′-methoxyacetophenone
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Synonyms:
Ethanone,1-(2-hydroxy-5-methoxyphenyl)-;Acetophenone,2′-hydroxy-5′-methoxy-;1-(2-Hydroxy-5-methoxyphenyl)ethanone;2-Hydroxy-5-methoxyacetophenone;2′-Hydroxy-5′-methoxyacetophenone;5-Methoxy-2-hydroxyacetophenone;2-Acetyl-4-methoxyphenol;1-(2-hydroxy-5-methoxyphenyl)ethanone;NSC 338218;2-Hydroxy-5-Methyloxyacetophenone;1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one
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CAS No:
2′-Hydroxy-5′-methoxyacetophenone Basic Attributes
166.176
166.17
211-882-3
338218
DTXSID40220765
2914509090
Safety Information
NONH for all modes of transport
3
R36/37/38
S26-S37/39-S36/37/39-S22
Xi:Irritant
P261-P280-P305 + P351 + P338
H315-H318-H335
|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2′-Hydroxy-5′-methoxyacetophenone Use and Manufacturing
To a suspension of 2’, 5’-dihydroxyacetophenone (100 mg, 0.66 mmol) and potassium carbonate (95 mg, 0.69 mmol) was added dimethyl sulfate (87 mg, 0.69 mmol), and the mixture was stirred at room temperature overnight. The reaction mixture was filtered and concentrated under reduced pressure. The resultant residue was treated with 2N NaOH and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane-EtOAc (10:1) to give 2’-hydroxy-5’-methoxyacetophenone in 40percent yield as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 11.9 (s, 1H), 7.18 (d, J = 2.8 Hz, 1H), 7.12 (dd, J = 8.8, 2.8 Hz, 1H), 6.93 (d, J = 8.8 Hz, 1H), 3.81 (s, 3H), 2.63 (s, 3H).General procedure: A suspension of 1a-1c (46 mmol) and aluminum chloride (69 mmol, 9 g) was stirred at 150 ℃. After 3.5 h the mixture was cooled to room temperature and the diluted hydrochloric acid was added to it slowly for quenching aluminum chloride until all solid disappeared. Then the solution was extracted with ethyl acetate (20 mL×3), and the combined organic layer was washed by saturated sodium chloride solution for three times, dried over anhydrous Na3.0 g (24 mmol) of p-methoxyphenol was dissolved in 24 ml of freshly distilled toluene solution, Under nitrogen, 1.5 ml of acetic anhydride and 12 ml of boron trifluoride diethyl ether were added in that order.Reflux 2h, to determine the end point of TLC, to be cooled to room temperature after the reaction solution, Slowly pour it into the ice water, a solid precipitation, filtration, drying, Recrystallization from absolute ethanol gave 2.6 g of a yellow solid in 66.67percent yield.
Computed Properties
Molecular Weight:166.17
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:166.062994177
Monoisotopic Mass:166.062994177
Topological Polar Surface Area:46.5
Heavy Atom Count:12
Complexity:167
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2′-Hydroxy-5′-methoxyacetophenone
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