Réaction #574075

Équation de réaction

1-(1,3-benzodioxol-5-yl)-1-butanol

mercaptoacetic acid

benzene

→

intended compound

Rendement 89.3%

[{1-(1,3-benzodioxol-5-yl)butyl}thio]acetic acid

Rendement 89.3%

Solvants

ether

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureunder reflux for 2 h
3. 3
   LavageAfter washing with water
4. 4
   workup.DISSOLUTIONthe product was redissolved in 750 ml of 1NNaOH
5. 5
   AutreThe solution thus obtained
6. 6
   Lavagewas washed with ether
7. 7
   Extractionextracted with 800 ml
8. 8
   LavageThe extract was washed with water
9. 9
   Séchagedried over magnesium sulfate
10. 10
    Concentrationconcentrated under reduced pressure
11. 11
    Autreto obtain 132 g of the crude product
12. 12
    AutreIt was purified

Mode opératoire

A mixture of 103 g of 1-(1,3-benzodioxol-5-yl)-1-butanol, 73.3 g of mercaptoacetic acid, 0.1 g of D-10-camphorsulfonic acid and 500 ml of benzene was heated under reflux for 2 h. 2,000 ml of ether was added to the reaction mixture. After washing with water, the product was redissolved in 750 ml of 1NNaOH and then in 100 ml thereof. The solution thus obtained was washed with ether and then with chloroform, acidified with concentrated hydrochloric acid and extracted with 800 ml and then 400 ml of ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to obtain 132 g of the crude product. It was purified according to silica gel column chromatography (ethyl acetate/hexane/formic acid=100:900:1) to obtain 127 g of the intended compound in the form of a colorless oil. This oil was crystallized from n-hexane to obtain 115 g of the titled compound as a white crystalline powder. It was found to have a melting point of 59° to 61° C.

Source