Acetic Acid → 7-Mercapto-1,4-benzodioxane-5-carboxylic acid

HRID 1659987Notes

Reaction equation

HRID 1659987 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([C:15]([OH:17])=[O:16])[C:8]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:14]=1)(=O)=O.C(O)(=O)C.[Sn].Cl>O>[SH:2][C:5]1[CH:6]=[C:7]([C:15]([OH:17])=[O:16])[C:8]2[O:13][CH2:12][CH2:11][O:10][C:9]=2[CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 64553167-(Chlorosulphonyl)-2,3-dihydro-1,4-benzodioxin-5-carboxylic acid

Product 1

HCID 205446947-Mercapto-1,4-benzodioxane-5-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

243 g of 7-chlorosulfonyl-1,4-benzodioxane-5-carboxylic acid and 654 cm3 of acetic acid were introduced into a balloon flask provided with an agitator and a condenser. The mixture was heated to 90° C. and then cooled to 45° C. 389 g of tin and 1,744 cm3 of hydrochloric acid were then added. The mixture was heated to 55°-60° C., cooled and poured into water. The precipitate was dried off, washed and dried. 166 g of 7-mercapto-1,4-benzodioxane-5-carboxylic acid were obtained (M.P.: 191°-192° C.; yield: 90%).

Workup

  1. customprovided with an agitator and a condenser
  2. temperaturecooled to 45° C
  3. temperatureThe mixture was heated to 55°-60° C.
  4. temperaturecooled
  5. customThe precipitate was dried off
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-dd89d8c58d684eb7bac91bf46f75dd54
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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