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| | 2-HYDROXY-5-BENZYLOXYACETOPHENONE Basic information |
| Product Name: | 2-HYDROXY-5-BENZYLOXYACETOPHENONE | | Synonyms: | 2-HYDROXY-5-BENZYLOXYACETOPHENONE;1-[2-Hydroxy-5-(phenylMethoxy)phenyl]ethanone;5'-Benzyloxy-2'-hydroxyacetophenone;Ethanone, 1-[2-hydroxy-5-(phenylMethoxy)phenyl]-;JR-13548, 1-(5-(Benzyloxy)-2-hydroxyphenyl)ethanone, 95%;Odatero Impurity 4;1-(2-Hydroxy-5-phenylmethoxyphenyl)ethanone - [H92760] | | CAS: | 30992-63-3 | | MF: | C15H14O3 | | MW: | 242.27 | | EINECS: | 202-110-6 | | Product Categories: | Aromatics Compounds;Aromatics | | Mol File: | 30992-63-3.mol |  |
| | 2-HYDROXY-5-BENZYLOXYACETOPHENONE Chemical Properties |
| Melting point | 64-66°C | | Boiling point | 391.2±27.0 °C(Predicted) | | density | 1.187±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,2-8°C | | solubility | Chloroform, Dichloromethane, Ethyl Acetate, Methanol | | pka | 10.52±0.20(Predicted) | | form | Solid | | color | Yellow |
| | 2-HYDROXY-5-BENZYLOXYACETOPHENONE Usage And Synthesis |
| 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 |
| | 2-HYDROXY-5-BENZYLOXYACETOPHENONE Preparation Products And Raw materials |
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