Hydrochloric Acid → 2-Chloro-4-(ethanesulfonyl)-3-hydroxybenzoic acid

HRID 1199240Notes

Reaction equation

HRID 1199240 reaction equation
[CH2:1]([S:3]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([Cl:15])[C:7]=1Cl)(=[O:5])=[O:4])[CH3:2].Cl.[OH-:18].[Na+]>>[Cl:15][C:8]1[C:7]([OH:18])=[C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27642492,3-Dichloro-4-(ethanesulfonyl)benzoic acid

Product 1

HCID 147454852-Chloro-4-(ethanesulfonyl)-3-hydroxybenzoic acid

Procedure

A solution of the 4-ethylsulfonyl-2,3-dichlorobenzoic acid prepared in Example 3 (0.35 mole) in 500 ml of 20% sodium hydroxide was heated at reflux for 7 hours. After cooling, the aqueous solution was acidified with concentrated hydrochloric acid and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, dried over magnesium sulfate, and concentrated in vacuo to afford the crude acid. Recrystallization of the crude acid from ethyl acetate afforded the desired pure acid as white crystals. m.p. 188°-192° C.

Workup

  1. temperatureat reflux for 7 hours
  2. temperatureAfter cooling
  3. extractionextracted twice with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford the crude acid
  7. customRecrystallization of the crude acid from ethyl acetate

Sources & evidence

ORD record
ord-5655b88e9f66410486b5c07749ceae5e
Source dataset
uspto-grants-1990_02
Patent number
US04898973

Reaction notes

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