Acetic Acid → 6-Mercaptochroman-8-carboxylic acid

HRID 1084929Notes

Reaction equation

HRID 1084929 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([C:15]([OH:17])=[O:16])[CH:14]=1)[O:11][CH2:10][CH2:9][CH2:8]2)(=O)=O.C(O)(=O)C.[Sn].Cl>O>[SH:2][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([C:15]([OH:17])=[O:16])[CH:14]=1)[O:11][CH2:10][CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5352426Tin atomHCID 20062876HCID 20062876, compound

Product 1

HCID 139835136-Mercaptochroman-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

238 g of 6-chlorosulphonylchroman-8- carboxylic acid and 645 ml of acetic acid were introduced into a 6-liter round-bottomed flask. The mixture was heated to 80° C. and 384 g of tin was added and the mixture was then cooled to 50° C. 1720 ml of hydrochloric acid (d=1.18) were then poured in dropwise, while maintaining the temperature between 55° and 60° C. first by cooling in an ice bath and then by heating in a water bath. Heating was then continued for 3 hours at 60° C. and the solution was poured into 6 liters of water. The precipitate formed was drained, washed with 1 liter of dilute hydrochloric acid followed by water and then air-dried.

Workup

  1. temperaturethe mixture was then cooled to 50° C
  2. temperaturewhile maintaining the temperature between 55° and 60° C. first
  3. temperatureby cooling in an ice bath
  4. temperatureby heating in a water bath
  5. temperatureHeating
  6. customThe precipitate formed
  7. washwashed with 1 liter of dilute hydrochloric acid
  8. customair-dried

Sources & evidence

ORD record
ord-ae73a964b6f74b7dbf889346437bb552
Source dataset
uspto-grants-1991_04
Patent number
US05006570

Reaction notes

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