Hydrochloric Acid → 2-[(2-Oxotetrahydro-3-furanyl)sulfanyl]benzoic acid

HRID 1659544

Reaction equation

HRID 1659544 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].C(=O)([O-])[O-].[Na+].[Na+].Br[CH:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20].Cl>O>[C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][CH:18]1[CH2:23][CH2:22][O:21][C:19]1=[O:20])([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic AcidHCID 10340Sodium CarbonateHCID 954632(3H)-Furanone, 3-bromodihydro-

Product 1

HCID 136222762-[(2-Oxotetrahydro-3-furanyl)sulfanyl]benzoic acidYield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 250 ml of water are dissolved 25 g of thiosalicylic acid and 60 g of sodium carbonate. Then, under ice-cooling, 38 g of α-bromo-γ-butyrolactone is added dropwise. The mixture is stirred at room temperature for 3 hours. The reaction mixture is made acidic with dilute hydrochloric acid and the resultant precipitate is recovered by filtration, rinsed with water and recrystallized from ethanol. By the above procedure there is obtained 32.5 g of α-[(2-carboxyphenyl)thio]-γ-butyrolactone as colorless prisms melting at 180°-182° C.

Workup

  1. temperatureThen, under ice-cooling
  2. filtrationthe resultant precipitate is recovered by filtration
  3. washrinsed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7de1dec7d360495e8718f7b62c4fa06e
Source dataset
uspto-grants-1981_12
Patent number
US04304784

Linked notes

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