4-Methoxyphenylacetone, also known as p-Anisylcetone, is an organic compound with the chemical formula of C10H12O2. It is white crystal powder. It is insoluble in water, but soluble in ethanol, ether, chloroform and benzene.
4-Methoxyphenylacetone can be chemically transformed through a variety of reactions. The following are some typical reaction properties:
1. Reactive methylene: 4-Methoxyphenylacetone can react with sulfuric acid and formic acid under acidic conditions to produce active methylene, and further react with aromatic amine to form N-aryl formamide analogues.
2. Ethanol esterification: 4-Methoxyphenylacetone can be esterified with ethanol under acid catalysis to obtain 4-Methoxyphenylacetate.
3. Hydrogenation: 4-Methoxyphenylacetone can be reduced to 4-Methoxyphenylacetone by catalytic hydrogenation.
4. Conduct electrophilic addition reaction: 4-Methoxyphenylacetone can conduct electrophilic addition reaction with electrophilic reagents (such as halogenated hydrocarbon, acyl halide, acid anhydride, etc.) to obtain different compounds.
5. Aromatic exchange reaction: 4-Methoxyphenylacetone can form new aromatic ketone analogues through ester exchange reaction with aromatic carboxylic acid.
These reactions show that 4-Methoxyphenylacetone has certain reactivity and can be used to synthesize a variety of organic compounds.
4-Methoxyphenylacetone can be synthesized by the aldol condensation reaction of acetophenone. The specific synthesis route is as follows:
1. Synthesis of 2,4-Dimethoxyacetophenone: reaction of acetophenone and methanol under the catalysis of sulfuric acid to obtain 2,4-Dimethoxyacetophenone.
2. Synthesis of 2,4-Dimethoxyacetophenone hydroxyaldehyde: 2,4-Dimethoxyacetophenone and formaldehyde are reacted in the presence of sodium hydroxide to obtain 2,4-Dimethoxyacetophenone hydroxyaldehyde.
3. Synthesis of 4-Methoxyphenylacetone: 2,4-dimethoxyphenylacetophenone hydroxyaldehyde is heated in the presence of hydrochloric acid to produce 4-Methoxyphenylacetone.
The detailed steps are as follows:
Step 1: Synthesis of 2,4-Dimethoxyacetophenone
Chemical reaction equation: C6H5CH2COCH3+2CH3OH+H2SO4 →(CH3O)2C6H3CH2C (O) CH3+2H2O+H2SO4
The ratio of acetophenone and methanol is 1:2, a small amount of sulfuric acid is added under stirring conditions as catalyst, and the reaction is conducted at room temperature for 12 hours. After the reaction, dilute the reaction solution with water, add saturated sodium carbonate solution for neutralization, and separate the organic phase with a separating funnel. Dry the organic phase with anhydrous sodium sulfate, and then remove the solvent with a rotary evaporator to obtain a white solid product of 2,4-dimethoxy acetophenone.
Step 2: Synthesis of 2,4-Dimethoxyacetophenone hydroxyaldehyde
Chemical reaction equation: (CH3O) 2C6H3CH2C(O)CH3+HCHO+NaOH → (CH3O)2C6H3CH(OH) CH2C(O)CH3+NaCl+H2O
Mix 2,4-Dimethoxyacetophenone and formaldehyde in molar ratio of 1:1.2, add appropriate amount of sodium hydroxide, and heat and stir in water bath for reaction for 12 hours. After the reaction, neutralize the reaction solution with saturated hydrochloric acid solution, and separate the organic phase with a separating funnel.
The following is the laboratory synthesis method of 4-Methoxyphenylacetone:
Chemical reaction equation: C6H5CH2COCH3+2CH3OH+H2SO4 → (CH3O)2C6H3CH2C(O) CH3+2H2O+H2SO4
(CH3O)2C6H3CH2C(O)CH3 + HCl → C10H12O2Cl2 + 2CH3OH
Experimental steps:
1. Synthesis of 2,4-Dimethoxyacetophenone:
Mix acetophenone (1 mol) and methanol (2 mol), add a small amount of sulfuric acid as catalyst, stir for reaction at room temperature for 12 hours, dilute the reaction solution with water, add saturated sodium carbonate solution for neutralization, and separate the organic phase with a separating funnel. Dry the organic phase with anhydrous sodium sulfate, and then remove the solvent with a rotary evaporator to obtain a white solid product of 2,4-dimethoxy acetophenone.
2. Synthetic 4-Methoxyphenylacetone:
Mix 2,4-dimethoxy acetophenone (1 mol) and formaldehyde (1.2 mol) according to the molar ratio, add a proper amount of sodium hydroxide, and heat and stir in a water bath for 12 hours. After the reaction, neutralize the reaction solution with saturated hydrochloric acid solution, and separate the organic phase with a separating funnel. Dry the organic phase with anhydrous sodium sulfate, and then remove the solvent with a rotary evaporator to obtain 4-Methoxyphenylacetone oily liquid product.
3. Purified 4-Methoxyphenylacetone:
Add 4-Methoxyphenylacetone oily liquid product into a small amount of hydrochloric acid to obtain 4-Methoxyphenylacetone hydrochloride precipitation, extract the precipitation with anhydrous ether, then dry the organic phase with anhydrous sodium sulfate, remove the solvent with a rotary evaporator, and obtain 4-Methoxyphenylacetone white solid product.
The above is the laboratory synthesis method of 4-Methoxyphenylacetone. It should be noted that necessary safety protection measures should be taken during the experiment and the operation should be carried out in strict accordance with the experimental steps.
The industrial synthesis of 4-Methoxyphenylacetone mainly includes the following two methods:
Method 1: Toluene was synthesized by carboxylation, reduction, acylation and formaldehyde condensation. The specific synthesis route is as follows:
Toluene+cobalt oxide 3 times → p-toluenoic acid
P-toluenoic acid+manganese/zinc → methyl p-toluenoic acid
Methyl p-toluene formate+nitric acid → methyl p-methoxybenzoate
Methyl p-methoxybenzoate+sodium hydroxide → p-methoxybenzaldehyde
P-methoxybenzaldehyde+acetone+hydrochloric acid → 4-Methoxyphenylacetone
Method 2: styrene was synthesized by hydroxymethylation, oxidation and acylation. The specific synthesis route is as follows:
Styrene+methanol+catalyst → p-methoxy styrene
P-methoxy styrene+oxidant → p-methoxy styrene aldehyde
P-Methoxystyrene aldehyde+oxidant → 4-Methoxyphenylacetone
Both of these two synthesis methods have certain advantages and disadvantages, but at present, the first method is mainly used for the production of 4-Methoxyphenylacetone in industry. The method uses low cost raw materials, mild reaction conditions and high reaction yield, and is suitable for large-scale industrial production.