Water → HCID 15526293, compound

HRID 904574Notes

Reaction equation

HRID 904574 reaction equation
[C:1]([O:6]C)(=O)/[CH:2]=[CH:3]/[CH3:4].[C:8](OC)(=[S:12])[CH:9](C)O.[CH3:15][O-:16].[Na+].[OH2:18].[C:19]1(C)C=CC=CC=1>C(O)(=O)C>[CH3:4][CH:3]1[CH:2]([C:15]([O:18][CH3:19])=[O:16])[C:1](=[O:6])[CH:8]([CH3:9])[S:12]1

Participants

7

Reactant 5

HCID 962WaterHCID 1140Toluene2×HCID 638132Methyl CrotonateHCID 10942334Sodium MethoxideHCID 86737304HCID 86737304, compound

Product 1

HCID 15526293HCID 15526293, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 83 g (0.83 mol) of methyl crotonate (Aldrich Chemical Company) and 100 g (0.83 mol) of methyl thiolactate (Helvetica Chemica Acta, Vol. 45, pages 1750-1765, 1962) in 800 ml of toluene is added dropwise to a stirred suspension of 64.8 g (1.2 mol) of sodium methoxide (Aldrich Chemical Company) in 500 ml of toluene. The suspension is stirred and refluxed for four and one-half hours, cooled, 500 ml of water is added and the mixture is made acidic by the addition of glacial acetic acid. The aqueous solution is extracted with toluene. The toluene layer is separated, washed successively with 200 ml of water, 200 ml of saturated sodium bicarbonate solution and 200 ml of water, dried over anhydrous Na2SO4, and the solution evaporated to give 90 g of tetrahydro-2,5-dimethyl-4-oxo-3-thiophenecarboxylic acid, methyl ester; bp 78°-80° C./0.04 mm.

Workup

  1. temperaturerefluxed for four and one-half hours
  2. temperaturecooled
  3. extractionThe aqueous solution is extracted with toluene
  4. customThe toluene layer is separated
  5. washwashed successively with 200 ml of water, 200 ml of saturated sodium bicarbonate solution and 200 ml of water
  6. dry with materialdried over anhydrous Na2SO4
  7. customthe solution evaporated

Sources & evidence

ORD record
ord-f067fa1ec0db4bc981bc9f3b4ae1d8df
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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