2-Mercaptobenzoic Acid → Sodium 2-sulfanylbenzoate

HRID 1287524Notes

Reaction equation

HRID 1287524 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[H-].[Na+:12]>COCCOC>[SH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[Na+:12]

Participants

4

Reactant 2

HCID 54432-Mercaptobenzoic AcidHCID 24758Sodium hydride

Product 1

HCID 23690429Sodium 2-sulfanylbenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 2-mercaptobenzoic acid (15.4 g, 0.1 mole) in 50 ml of 1,2-dimethoxyethane (DME) was slowly added, with cooling, to a stirred suspension of 0.1 mole of sodium hydride in DME, the suspension having been prepared by washing 4.2 grams of a 57% oil dispersion with dry n-hexane (3 times) and replacing the last wash with dry 1,2-dimethoxyethane (50 ml). Cooling was necessary to maintain the temperature below 25°C. The resultant suspension was heated at 50°C for 2 hours, cooled to 0°C and filtered. The solid was washed well with cold DME (ca. 50 ml) and dried under vacuum overnight to yield sodium 2-mercaptobenzoate: 17.6 g (100% yield);

Workup

  1. customthe suspension having been prepared
  2. washby washing 4.2 grams of a 57% oil dispersion with dry n-hexane (3 times)
  3. washlast wash with dry 1,2-dimethoxyethane (50 ml)
  4. temperatureCooling
  5. temperatureto maintain the temperature below 25°C
  6. temperaturecooled to 0°C
  7. filtrationfiltered
  8. washThe solid was washed well with cold DME (ca. 50 ml)
  9. customdried under vacuum overnight

Sources & evidence

ORD record
ord-c303460bb8464f50bb0787f26390e585
Source dataset
uspto-grants-1976_10
Patent number
US03984573

Reaction notes

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