Hydrochloric Acid → HCID 178427263, compound

HRID 1606609Notes

Reaction equation

HRID 1606609 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])C(S)=[CH:7][C:3]=1[C:4](O)=O.[OH-].[Na+].[S:15](OC)(OC)(=O)=O.Cl.[CH2:23]([OH:25])[CH3:24]>O>[Cl:11][C:9]1[CH:10]=[C:2]([Cl:1])[C:3]([CH3:7])=[CH:4][C:24]=1[C:23]([OH:25])=[S:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 215439732,4-Dichloro-5-mercaptobenzoic acid

Product 1

HCID 178427263HCID 178427263, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 2,4-dichloro-5-mercaptobenzoic acid (30 g.; 0.135 mole) in 50% aqueous ethanol (500 ml.) and sufficient 10N sodium hydroxide to attain a pH of 9 is heated to reflux and treated dropwise with dimethyl sulfate (26 g.; 0.206 mole) during a two hour period. The pH is maintained at 9 during the addition. The reaction mixture then is cooled, diluted with water (1 liter) and acidified with dilute hydrochloric acid, yielding 30 g.; (94%) of 2,4-dichloro-5-methylthiobenzoic acid, m.p. 187° C. after recrystallization from nitromethane.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. temperatureThe pH is maintained at 9 during the addition
  4. temperatureThe reaction mixture then is cooled
  5. customyielding 30 g
  6. custom(94%) of 2,4-dichloro-5-methylthiobenzoic acid, m.p. 187° C. after recrystallization from nitromethane

Sources & evidence

ORD record
ord-4c4c794c0a41497abb17a2fb99c38a5b
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

Loading…