136192-85-3

Basic information

• Product Name: methyl 1-hydroxy-6-acetylbenzoate
• Synonyms: methyl 1-hydroxy-6-acetylbenzoate
• CAS NO: 136192-85-3
• Molecular Weight: 194.187
• Mol File: 136192-85-3.mol

Chemical Properties

• CAS DataBase Reference: methyl 1-hydroxy-6-acetylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-hydroxy-6-acetylbenzoate(136192-85-3)
• EPA Substance Registry System: methyl 1-hydroxy-6-acetylbenzoate(136192-85-3)

Safety Data

• Hazardous Substances Data: 136192-85-3(Hazardous Substances Data)

Upstream product

• 179678-23-0 2-acetyl-6-amino-benzoic acid methyl ester 
• 85865-57-2 2-(Methoxycarbonyl)-3-methoxyacetophenone 
• 121-71-1 3-Hydroxyacetophenone 
• 67-56-1 methanol 
• 99512-66-0 O-acetyl-salicylic acid 
• 179678-21-8 (2-methoxycarbonyl-3-nitro-benzoyl)-malonic acid diethyl ester 
• 147411-66-3 2-Benzyloxy-6-(1,1-dimethoxy-ethyl)-benzoic acid methyl ester 
• 149220-60-0 1-Benzyloxy-3-(1,1-dimethoxy-ethyl)-benzene 
• 143613-10-9 2-[3-(benzyloxy)phenyl]-2-methyl-1,3-dioxolane 
• 143613-14-3 methyl 2-(benzyloxy)-6-(2-methyl-1,3-dioxolan-2-yl)benzoate 
• 179678-22-9 2-acetyl-6-nitro-benzoic acid methyl ester 
• 179678-24-1 2-acetyl-6-methoxy-benzoic acid 
• 13619-70-0 2-acetyl-6-nitrobenzoic acid 
• 34068-01-4 1-[3-(phenylmethoxy)phenyl]ethan-1-one 

Downstream Products

• 136192-81-9 Methyl 6-[1-(methyloximino)ethyl]salicylate 
• 136192-67-1 Methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate 
• 136192-66-0 Benzyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate 
• 186759-90-0 1-[3-hydroxy-2-(imidazole-1-carbonyl)-phenyl]-ethanone O-methyl-oxime 
• 136192-82-0 6-[1-(Methyloximino)ethyl]salicylic acid 

Relevant articles and documents

Method for synthesizing herbicide pyriminobac-methyl in paddy field

The invention belongs to the field of fine chemical engineering, and particularly relates to a preparation method of herbicide pyriminobac-methyl for a paddy fields. The preparation method comprises the following steps: synthesizing 3-hydroxy phthalic anhydride by using 3-chlorophthalic anhydride as a new raw material, protecting carbonyl by using diethyl malonate, hydrolyzing to obtain 2-acetyl-6-hydroxy benzoic acid, and esterifying to obtain 2-acetyl-6-hydroxy methyl benzoate; then carrying out imidization reaction with methoxyamine hydrochloride to obtain 2-hydroxy-6-(1-methoxy iminoethyl-methyl)-benzoate, and finally, condensing with 2-tosyl-4, 6-dimethoxypyrimidine to obtain pyriminobac-methyl. In the process of preparing pyriminobac-methyl, high-risk reagents such as n-butyllithiumare avoided, a large amount of wastewater generated by diazotization is avoided, the income is increased, and the environment is protected.

Studies of the New Herbicide KIH-6127. Part I. Novel Synthesis of Methyl 6-Acetylsalicylate as a Key Synthetic Intermediate for the Preparation of 6-Acetyl Pyrimidin-2-yl Salicylates and Analogues

A novel synthesis of methyl 6-acetylsalicylate as a key synthetic intermediate for methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate (KIH-6127) was studied, and directed at 6-substituted pyrimidin-2-yl salicylate herbicides and their analogues. Three synthetic approaches were successful: a modification of the Sandmeyer reaction of 6-acetylanthranilate (Method A), a direct ring-opening reaction of 3-methylphthalide using potassium permanganate, and magnesium nitrate (Method B), and a regioselective ortholithiation of the protected 3-hydroxyacetophenone (Method C). These methods were applicable for the synthesis of various 6-acyl salicylates.

A practical synthesis of 6-acetylsalicylic acid methyl ester

A new and efficient synthesis of the title compound is reported. The method includes a regioselective ortho-lithiation step in none polar solvents at an ambient temperature and the overall yield for 5 steps is more than 70% from a commercially available 3-hydroxyacetophenone.