Hydrochloric Acid → 2-(Isopropylthio)benzoic acid

HRID 1928560Notes

Reaction equation

HRID 1928560 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH:11](Br)([CH3:13])[CH3:12].[OH-].[K+].Cl>C(O)C>[CH:11]([S:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic AcidHCID 63582-BromopropaneHCID 14797Potassium Hydroxide

Product 1

HCID 47779552-(Isopropylthio)benzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of thiosalicylic acid (16.7 g; 109 mmol; Fluka) and isopropyl bromide (20.0 g; 163 mmol) in ethanol (125 ml) were added slowly, with vigorous stirring, KOH pellets (17.3 g; 433 mmol). After stirring for 6 h, the reaction mixture was poured into water-ice mixture (1200 ml) and acidified with concentrated hydrochloric acid (approx. 50 ml). The precipitated product was filtered off, washed with 50% aqueous ethanol (2×100 ml) and dried under reduced pressure. Yield 6.4 g (30%).

Workup

  1. filtrationThe precipitated product was filtered off
  2. washwashed with 50% aqueous ethanol (2×100 ml)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-ea84b1db549c42b7a7dee3a7dfd26f06
Source dataset
uspto-grants-2012_05
Patent number
US08183382B2

Reaction notes

Loading…