Chloroacetic Acid → 2-Thiopheneacetic acid

HRID 323522Notes

Reaction equation

HRID 323522 reaction equation
[OH-].[Na+].[SH:3][C:4]1O[CH:6]=[CH:7][CH:8]=1.Cl[CH2:10][C:11]([OH:13])=[O:12].Cl>O.CO.C(O)C>[C:11]([CH2:10][C:4]1[S:3][CH:6]=[CH:7][CH:8]=1)([OH:13])=[O:12]

Participants

8

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 83164Furan-2-thiol

Product 1

HCID 159702-Thiopheneacetic acidYield 74%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

Aqueous solution of sodium hydroxide 8.8 g (0.22 mol) in water of 15 ml was added drop by drop to mixture of 2-mercapto furan 20.0 g (0.20 mol), chloroacetic acid 27.0 g (0.22 mol) and ethanol 300 ml with stirring at room temperature. After 20 minutes of stirring it was heated to 50° C., and further aqueous solution of sodium hydroxide 8.8 g (0.22 mol) in 15 ml of water was added slowly drop by drop. After stirring for 3 hours at 50° C., it was cooled to room temperature, and water was added till reaction liquid became uniform. Hydrochloric acid was added for neutralization. Prepared crystal was collected by filtration and 23.5 g (0.148 mol) of 2-carboxymethylthiofuran was obtained by recrystallization in methanol. Synthesis of yield 74%.

Workup

  1. stirringAfter 20 minutes of stirring it
  2. temperaturewas heated to 50° C.
  3. stirringAfter stirring for 3 hours at 50° C.
  4. temperatureit was cooled to room temperature
  5. customPrepared crystal
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-dcdec67cd9f1427fbb06058a7c519036
Source dataset
uspto-grants-2001_04
Patent number
US06214533B1

Reaction notes

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