Ethyl sulfate anion → 7-Ethylthio-1,4-benzodioxane-5-carboxylic acid

HRID 2286923Notes

Reaction equation

HRID 2286923 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[CH2:15](OS([O-])(=O)=O)[CH3:16]>O>[CH2:15]([S:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1)[CH3:16]

Participants

4

Reactant 2

HCID 3804841Ethyl sulfate anionHCID 205446947-Mercapto-1,4-benzodioxane-5-carboxylic acid

Product 1

HCID 205447267-Ethylthio-1,4-benzodioxane-5-carboxylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

166 g of 7-mercapto-1,4-benzodioxane-5-carboxylic acid, 242 cm3 of water, 216 cm3 of soda lye and 181 g of ethylsulfate were introduced into a balloon flask provided with a condenser. The mixture was heated under reflux and then cooled. The solution was poured into 1.3 l of water, filtered and treated with 110 cm3 of hydrochloric acid. The precipitate was dried off, washed with water and dried. 152 g of 7-ethylthio-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 153°-154° C.; yield: 81%).

Workup

  1. customprovided with a condenser
  2. temperatureThe mixture was heated
  3. temperatureunder reflux
  4. temperaturecooled
  5. filtrationfiltered
  6. additiontreated with 110 cm3 of hydrochloric acid
  7. customThe precipitate was dried off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-171d49c82568481cba9ad003945c8339
Source dataset
uspto-grants-1981_05
Patent number
US04268512

Reaction notes

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