Methyl 2-chloroacrylate → 3-Hydroxy-thiophene-2-carboxylic acid methyl ester

HRID 621786Notes

Reaction equation

HRID 621786 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[Na].Cl[C:9](=[CH2:14])[C:10](OC)=[O:11]>CO>[OH:11][C:10]1[CH:9]=[CH:14][S:3][C:2]=1[C:1]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 6659Methyl 2-chloroacrylateHCID 16907Methyl ThioglycolateHCID 5360545Sodium

Product 1

HCID 5811273-Hydroxy-thiophene-2-carboxylic acid methyl esterYield 74.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of methyl thioglycolate (19.2 g, 181 mmoles) in methanol (100 mL) is added to a solution of sodium (8.0 g, 348 mmoles) in methanol (100 mL) with stirring, and cooling with an ice bath. A solution of methyl α-chloroacrylate (22.1 g, 183 mmoles) in methanol (25 mL) is then added at such a rate that the temperature does not exceed 30° C. After 1 hour at ambient temperature, the methanol is removed under reduced pressure. The residue is dissolved in water, acidified with HCl and steam distilled until the distillate is clear. The distillate is cooled and shaken, and the resulting precipitate filtered off, rinsed with water and dried to afford the product (21.3 g); mp 43°-45° C.

Workup

  1. temperaturecooling with an ice bath
  2. customdoes not exceed 30° C
  3. customthe methanol is removed under reduced pressure
  4. dissolutionThe residue is dissolved in water
  5. distillationdistilled until the distillate
  6. temperatureThe distillate is cooled
  7. stirringshaken
  8. filtrationthe resulting precipitate filtered off
  9. washrinsed with water
  10. customdried

Sources & evidence

ORD record
ord-525ed6eaafc74e0caa804b4e0b185dc4
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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