Hydrochloric Acid → Ethyl 3-hydroxy-5-methyl-2-thiophenecarboxylate

HRID 1200098Notes

Reaction equation

HRID 1200098 reaction equation
Cl.[C:2]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].[SH:11][CH2:12][C:13](OCC)=O.[OH-].[K+]>>[OH:5][C:4]1[CH:6]=[C:12]([CH3:13])[S:11][C:3]=1[C:2]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8868Ethyl AcetoacetateHCID 12185Ethyl ThioglycolateHCID 14797Potassium Hydroxide

Product 1

HCID 54730138Ethyl 3-hydroxy-5-methyl-2-thiophenecarboxylate

Procedure

Dry hydrogen chloride gas was bubbled through a mixture of ethyl acetoacetate (0.2 moles) and ethyl 2-mercaptoacetate (b 0.4 moles) at -10° C. until saturated. The oil was allowed to stand 4 days at room temperature. Then, 350 ml of 2N ethanolic KOH, was added drop-wise. The resultant mixture was added to 2 liters of ice-water, and acidified with 6M HCl until the pH was approximately 1. The precipitated oil was extracted with benzene, washed with water and dried with sodium sulphate. After removal of solvent the residue was distilled, b.p. 70°-75° C. (0.5 mm).

Workup

  1. extractionThe precipitated oil was extracted with benzene
  2. washwashed with water
  3. dry with materialdried with sodium sulphate
  4. customAfter removal of solvent the residue
  5. distillationwas distilled

Sources & evidence

ORD record
ord-657da6d11e8e4f36b3a4e7996927007d
Source dataset
uspto-grants-1990_02
Patent number
US04904686

Reaction notes

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