Hydrochloric Acid → HCID 54440692, compound

HRID 1732941Notes

Reaction equation

HRID 1732941 reaction equation
CO[C:3](=[S:11])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[O:12](C)[Na].CO.Cl>>[CH3:10][O:9][C:7]([CH:6]1[CH:5]([OH:12])[CH:4]=[CH:3][S:11]1)=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 54249997HCID 54249997, compoundHCID 178501943HCID 178501943, compound

Product 1

HCID 54440692HCID 54440692, compoundYield 88%

Conditions

Temperature
5 °C

Procedure

192 Parts of 3-methoxycarbonylmethyl-thiopropionic acid methyl ester are added, in the course of 30 minutes, to a solution of 360 parts of a 30 percent strength by weight NaOCH3 /MeOH solution at 5° C. The resulting solution is stirred for one hour at 5° C. and then poured onto a mixture of 200 parts of concentrated hydrochloric acid and 1,000 parts of finely crushed ice. The oily layer which separates out is removed and the aqueous phase is extracted with three times 100 parts by volume of methylene chloride. The combined organic phases are extracted with three times 100 parts by volume of 5 percent strength by weight NaHCO3 solution, dried with sodium sulfate and evaporated. The residue is distilled under reduced pressure. 140 parts (88% of theory) of 3-hydroxy-dihydrothiophene-2-carboxylic acid methyl ester of boiling point 72°-73° C/0.14 mbar are obtained.

Workup

  1. customThe oily layer which separates out is removed
  2. extractionthe aqueous phase is extracted with three times 100 parts by volume of methylene chloride
  3. extractionThe combined organic phases are extracted with three times 100 parts by volume of 5 percent strength by weight NaHCO3 solution
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-2ed80803f7c44003b3eb105d28b83029
Source dataset
uspto-grants-1980_12
Patent number
US04239897

Reaction notes

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