Acetic Acid → HCID 178427262, compound

HRID 2303443Notes

Reaction equation

HRID 2303443 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[S:8])=[CH:5][C:4]=1[CH3:12].C(O)(=O)C.Br.C([O-])([O-])=O.[Na+].[Na+]>O>[OH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[S:8])=[CH:5][C:4]=1[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 178491637HCID 178491637, compound

Product 1

HCID 178427262HCID 178427262, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Methoxy-3-methylthiobenzoic acid (0.5 g, 2.5 mmol) is suspended in 7 ml of a mixture of glacial acetic acid and 48% strength HBr (1+1). The reaction mixture is stirred under reflux for 6 h. The reaction mixture is cooled to RT and added to 20 ml of H2O. The aqueous solution is adjusted to pH=2 using 10% strength Na2CO3 solution and extracted 4× using 20 ml of diethyl ether each time. The organic extracts are combined, washed 2× with saturated NaCl solution, dried over Na2SO4 and concentrated: dirty-brown oil, which crystallizes on allowing to stand at RT. The crystallizate is dried, washed with H2O with stirring, filtered off and dried. Yield: 240 mg (52%).

Workup

  1. temperatureunder reflux for 6 h
  2. extractionextracted 4×
  3. washwashed 2× with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customdirty-brown oil, which crystallizes
  7. customto stand at RT
  8. customThe crystallizate is dried
  9. washwashed with H2O
  10. stirringwith stirring
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-431b707c34994ee6b5f36545237f81bf
Source dataset
uspto-grants-2002_08
Patent number
US06432988B1

Reaction notes

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