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

HRID 1691343Notes

Reaction equation

HRID 1691343 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-795a64866fda4a61a73792f38494fb28
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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