Ethanol → HCID 53978036, compound

HRID 2256979Notes

Reaction equation

HRID 2256979 reaction equation
[Cl:1][C:2]1[C:3]([SH:12])=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[Cl:1][C:2]1[C:3]([SH:12])=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([O:7][CH2:18][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 54321297HCID 54321297, compound

Product 1

HCID 53978036HCID 53978036, compound

Procedure

A solution of 3,4-dichloro-2-mercaptobenzoic acid (17.78 g) and concentrated sulphuric acid (3.75 ml) in ethanol was heated at reflux for 20 hours. After cooling the mixture was evaporated and the residue suspended in dichloromethane, washed with water, sodium bicarbonate, water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness. The residue was triturated with hexane to give ethyl 3,4-dichloro-2-mercaptobenzoate (7.96 g) as a yellow solid NMR (CDCl3) 1.3(t,3H), 4.25(q,2H), 6.75(s,1H), 7.15(d,1H), 7.8(d,1H).

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureAfter cooling the mixture
  3. customwas evaporated
  4. washwashed with water, sodium bicarbonate, water
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customThe residue was triturated with hexane

Sources & evidence

ORD record
ord-1505da4d3c4c412faac05c5ac8a917fa
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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