| Identification | Back Directory | [Name]
2-HYDROXY-5-BENZYLOXYACETOPHENONE | [CAS]
30992-63-3 | [Synonyms]
2-HYDROXY-5-BENZYLOXYACETOPHENONE
5'-Benzyloxy-2'-hydroxyacetophenone
1-[2-Hydroxy-5-(phenylMethoxy)phenyl]ethanone
Ethanone, 1-[2-hydroxy-5-(phenylMethoxy)phenyl]- | [EINECS(EC#)]
202-110-6 | [Molecular Formula]
C15H14O3 | [MDL Number]
MFCD00598842 | [MOL File]
30992-63-3.mol | [Molecular Weight]
242.27 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Solid | [Melting point ]
64-66°C | [Boiling point ]
391.2±27.0 °C(Predicted) | [density ]
1.187±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform, Dichloromethane, Ethyl Acetate, Methanol | [form ]
Solid | [pka]
10.52±0.20(Predicted) | [color ]
Yellow |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
2-Hydroxy-5-benzyloxyacetophenone (cas# 30992-63-3) is a compound useful in organic synthesis. | [Preparation]
Preparation by reaction of benzyl chloride with quinacetophenone in refluxing acetone in the presence of potassium carbonate,
with potassium iodide (85%) ;
without potassium iodide (31%). | [Synthesis]
The second alternative method first employs benzyl groups to protect the hydroxyl functional group in 2,5-dihydroxyacetophenone, followed by an O-alkylation reaction under the same conditions to give acetophenone derivatives (1-6) in high yields (95%). Next, the acetophenone derivatives (1-6) were converted by the Vilsmeier-Haack reaction under standard conditions (70% yield) to the products (1-7) which were previously synthesized by other methods. Finally, the product (1-7) was subjected to Knoevenagel condensation reaction with diethyl malonate to give the target diester (1-8) in high yield (94%). Based on the analysis of the results of Scheme 2, it can be observed that both methods can be used for the synthesis of intermediates (1-7) from 2,5-dihydroxyacetophenone (1-4) in overall yields of 42% and 66%, respectively. However, the second method showed superior performance in terms of yield. | [References]
[1] Patent: WO2018/156459, 2018, A1. Location in patent: Page/Page column 22; 23
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 1, p. 249 - 266
[3] Patent: US2007/88160, 2007, A1. Location in patent: Page/Page column 10-11
[4] Patent: US2010/22770, 2010, A1. Location in patent: Page/Page column 5-6
[5] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1410 - 1414 |
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