The Willgerodt reaction with 2-acetylthiophene was written by Dann, Otto;Distler, Harry. And the article was included in Chemische Berichte in 1951.Recommanded Product: 19432-68-9 This article mentions the following:
Because the addition of RCH2CONH2 (I) (R = S.CH:CH.CH:C throughout the abstract) to the nutrient in the biosynthesis of penicillia gave a product with a highly increased activity and 2-thienylmethylpenicillin showed indications of permanent action, a synthesis of I by the Willgerodt reaction is carried out. Heating 10 g. RCOMe, 18 cc. dioxane, 22 cc. concentrated NH4OH, 15 g. S, and 12 cc. yellow (NH4)2Sx in a bomb within 1 hr. at 142°, keeping the mixture 3.25 hrs. at 142°, raising the temperature the last 1/4 hr. to 152°, evaporating the contents of 3 runs on the water bath, and extracting the residue with hot H2O gives 68% I, m. 146.5°. Refluxing 700 mg. I in 15 cc. 10% KOH 12 hrs. and acidifying with concentrated HCl give 300 mg. RCH2CO2H (II), m. 64°. Refluxing 6 g. II with 30 g. MeOH and 1 g. concentrated HCl 5 hrs. gives 82% RCH2CO2Me, b25 119-22°, nD19.5 1.5243. Adding dropwise 86 g. SnCl4 over a period of 2 hrs. to 37.3 g. 2,5-dimethylthiophene, 26 g. AcCl, and 400 g. C6H6 with ice-NaCl cooling and stirring, and stirring the mixture 3 hrs. at 25-30° give 91% (with AlCl3 in CS2, 60%) 2,5-dimethyl-3-acetylthiophene (III), b8 96-105°, nD24 1.5404 (semicarbazone, m. 211°). Refluxing 4.5 hrs. 132 g. III, 120 g. morpholine, and 45 g. S, pouring the mixture into 100 cc. EtOH-Me2CO (1:1), and cooling with ice-NaCl give 56.8% 3-(2,5-dimethylthienyl)thioacetomorpholide (IV), shiny slightly yellow leaflets, m. 76°. Refluxing 12 hrs. 124 g. IV with 120 g. KOH in 1.2 l. MeOH, evaporating the mixture on a water bath to dryness, dissolving the residue in 700 cc. hot H2O, washing the solution with CS2 and ether, and acidifying with dilute H2SO4 give 50% 3-(2,5-dimethylthienyl)acetic acid, b2.6 152-3°. In the experiment, the researchers used many compounds, for example, Methyl 2-thienylacetate (cas: 19432-68-9Recommanded Product: 19432-68-9).
Methyl 2-thienylacetate (cas: 19432-68-9) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Recommanded Product: 19432-68-9
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics