Preparation method of 2,2'-dihydroxy diphenyl ketone compound
A technology of dihydroxybenzophenone and compounds, which is applied in the field of synthesis of ketone acyclic compounds, can solve the problems of expensive Grignard reagents and high raw material requirements, and achieve the effect of easy-to-obtain raw materials, high purity and high yield
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Embodiment 1
[0055] Example 1: Preparation of 5-methyl-3-[5-methyl-2-hydroxyphenyl]benzofuran-2-(3hydro)-one (p-methyllactone)
[0056] Put 21.6g of p-methylphenol (0.2mol), 9.2g of glyoxylic acid monohydrate (0.1mol) and 0.3g of p-toluenesulfonic acid in a 500ml three-necked flask, add 200ml of toluene, heat it to dissolve completely and then use a magnetic stirring belt The water was refluxed and reacted for 6 hours. The reaction was followed in the liquid phase. After the reaction was complete, the solvent was evaporated to dryness to obtain a yellow-brown solid, and then recrystallized from methanol to obtain a pale yellow solid 22.5g, namely 5-methyl-3-[5-methyl- 2-Hydroxyphenyl]benzofuran-2-(3hydro)-one, abbreviated as methyl lactone, the liquid phase purity of the methyl lactone is 98.3%, and the yield is 90.1%.
[0057] Product structure verification (see Figure 1A-1E ):
[0058] 1 HNMR(δ, ppm, 400MHz, CDCl 3 ): 2.239(s, 3H, CH 3 ); 2.321(s,3H,CH 3 ); 4.983(s,1H); 5.059(s,1H); 6.750(d,1...
Embodiment 2
[0063] Example 2: Preparation of 5-ethyl-3-[5-ethyl-2-hydroxyphenyl]benzofuran-2-(3hydro)-one (p-ethyl lactone)
[0064] Put 24.4g of p-ethylphenol (0.2mol), 9.2g of glyoxylic acid monohydrate (0.1mol) and 0.3g of p-toluenesulfonic acid in a 500ml three-necked flask, add 200ml of toluene, heat it to dissolve completely and then use a magnetic stirring belt The water was refluxed and reacted for 6 hours, and the reaction was followed in the liquid phase. After the reaction was completed, the solvent was evaporated to obtain a yellow-brown solid, and then recrystallized with ethanol to obtain a pale yellow solid 25.6g, namely 5-ethyl-3-[5-ethyl-2 -Hydroxyphenyl]benzofuran-2-(3hydro)-one, abbreviated as ethyl lactone, the liquid phase purity of the ethyl lactone is 98.5%, and the yield is 92.0%.
[0065] Product structure verification (see Figure 2A-2E ):
[0066] 1 HNMR(δ, ppm, 400MHz, CDCl 3 ):1.182(m,6H,CH 3 ); 2.536(q,2H); 2.613(q,2H); 4.677(s,1H); 5.081(s,1H).6.763(d,1H,J=8,Ar-H)...
Embodiment 3
[0071] Example 3: Preparation of 5-isopropyl-3-[5-isopropyl-2-hydroxyphenyl]benzofuran-2-(3hydro)-one (p-isopropyl lactone)
[0072] Put 27.2g of p-isopropylphenol (0.2mol), 9.2g of glyoxylic acid monohydrate (0.1mol) and 0.3g of p-toluenesulfonic acid in a 500ml three-necked flask, add 200ml of toluene, heat to completely dissolve and stir magnetically The reaction was refluxed with water for 6 hours, and the reaction was followed in the liquid phase. After the reaction was completed, the solvent was evaporated to dryness to obtain a yellow-brown solid, and then recrystallized with ethanol to obtain a pale yellow solid 27.3g, namely 5-isopropyl-3-[5-isopropyl 2-hydroxyphenyl]benzofuran-2-(3hydro)-one, referred to as propyl lactone, the liquid phase purity of the propyl lactone is 98.7%, and the yield is 89.2%.
[0073] Product structure verification (see Figure 3A-3E ):
[0074] 1 HNMR(δ, ppm, 400MHz, CDCl 3 ): 1.170 (m, 6H); 1.227 (d, 6H, J = 6.8); 2.798 (m, 1H); 2.903 (m, 1H); 5...
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