Potassium Carbonate → 3-(mercaptomethyl)benzoic acid

HRID 926751Notes

Reaction equation

HRID 926751 reaction equation
C([S:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[SH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 860892063-(Acetylthiomethyl)benzoic acid

Product 1

HCID 113211893-(mercaptomethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 500-mL round bottom flask, was placed a solution of 3-(acetylthiomethyl)benzoic acid (16.4 g, 78.10 mmol, 1.00 equiv) in methanol (150 mL), and a solution of potassium carbonate (26.9 g, 194.93 mmol, 2.50 equiv) in water (70 mL). The resulting solution was stirred for 4 h at 60° C. The resulting mixture was concentrated under vacuum, diluted with 200 mL of water, and then adjusted to pH 3 with 10% hydrochloric acid. The mixture was extracted with 3× (100/20 mL) of ethyl acetate/tetrahydrofuran and the organic layers combined, washed with 1×100 mL of brine, then dried over sodium sulfate and concentrated under vacuum. This resulted in 12 g (91%) of 3-(mercaptomethyl)benzoic acid as a brown solid.

Workup

  1. customInto a 500-mL round bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. additiondiluted with 200 mL of water
  4. extractionThe mixture was extracted with 3× (100/20 mL) of ethyl acetate/tetrahydrofuran
  5. washwashed with 1×100 mL of brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 12 g (91%) of 3-(mercaptomethyl)benzoic acid as a brown solid

Sources & evidence

ORD record
ord-578240aba41047ad9d7190d21351c02a
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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