Methyl Methacrylate → Methyl tetrahydro-4-methyl-3-oxo-2-thiophenecarboxylate

HRID 1680157Notes

Reaction equation

HRID 1680157 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:6])=[CH2:5].[CH3:8][O:9][C:10](=[O:13])[CH2:11][SH:12].N1CCCCC1.C[O-].[Na+]>CO>[CH3:8][O:9][C:10]([CH:11]1[C:3](=[O:2])[CH:4]([CH3:6])[CH2:5][S:12]1)=[O:13]

Participants

6

Reactant 4

HCID 6658Methyl MethacrylateHCID 8082PiperidineHCID 16907Methyl ThioglycolateHCID 10942334Sodium Methoxide

Product 1

HCID 10487456Methyl tetrahydro-4-methyl-3-oxo-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 g (1 mole) of methacrylic acid methyl ester are added dropwise to 106 g of thioglycolic acid methyl ester and 1 ml of piperidine. The reaction mixture is added dropwise to a solution of 40 g of sodium methylate in 200 ml of methanol. The mixture is stirred for a further half an hour, poured onto water, acidified and extracted with methylene chloride and the organic phase is washed with water and dried with sodium sulfate. After distillation, 4-methyl-3-oxotetrahydro-2-thiophencarboxylic acid methyl ester is obtained (bp. 110° to 115°/14 Pascal).

Workup

  1. additionpoured onto water
  2. extractionextracted with methylene chloride
  3. washthe organic phase is washed with water
  4. dry with materialdried with sodium sulfate
  5. distillationAfter distillation

Sources & evidence

ORD record
ord-00d3c601c26e409cba822f1b9244c5a5
Source dataset
uspto-grants-1981_06
Patent number
US04272507

Reaction notes

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