Hydrochloric Acid → 4-[(Phenylsulfanyl)methyl]benzoic acid

HRID 1891944Notes

Reaction equation

HRID 1891944 reaction equation
Br[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[S-:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na+].Cl>C(O)C>[C:13]1([S:12][CH2:2][C:3]2[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 225994-(Bromomethyl)benzoic acidHCID 4110039Sodium benzenethiolate

Product 1

HCID 8758244-[(Phenylsulfanyl)methyl]benzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(bromomethyl)benzoic acid (10 g, 46.5 mmol), sodium thiophenoxide (6.15 g, 46.5 mmol), and ethanol (100 mL) was stirred for 1.5 hours under reflux. This mixture was cooled to room temperature and acidified with 1 N hydrochloric acid. The precipitate thus produced was collected, dissolved in ethyl acetate, and washed with water. The organic layer was concentrated under a reduced pressure to obtain the title compound (10 g). The title compound was used in the following reaction without any further purification.

Workup

  1. temperatureunder reflux
  2. customThe precipitate thus produced
  3. customwas collected
  4. dissolutiondissolved in ethyl acetate
  5. washwashed with water
  6. concentrationThe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-c2e06231ad674474a4a3f042f6cb97fe
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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