Sulfuric Acid → HCID 14330444, compound

HRID 2292155Notes

Reaction equation

HRID 2292155 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][S:7][C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[C:9]=1[CH2:15][C:16]([O-:18])=[O:17])=[O:5])[CH3:2].[C:19](OC(=O)C)(=[O:21])[CH3:20].S(=O)(=O)(O)O.[CH3:31][CH2:32]OCC>C(O)(=O)C.O>[C:19]([O:14][C:10]1[C:9]([CH2:15][C:16]([O:18][CH2:31][CH3:32])=[O:17])=[C:8]([S:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:13]=[CH:12][CH:11]=1)(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 21276985HCID 21276985, compound

Product 1

HCID 14330444HCID 14330444, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a solution of α-(2-ethoxycarbonylmethylthio-6-oxocyclohex-1-enyl)acetate (156 g) in acetic acid (500 mL) is added acetic anhydride (750 mL). The solution is heated to 100° and a solution of sulfuric acid (53 g) in acetic acid (250 mL) is added dropwise. After addition is completed, the solution is heated until gas evolution ceases and the solvent is then removed in high vacuo to yield an oil which is mixed with ether and water. The layers are separated and the organic layer is washed with water, saturated sodium bicarbonate until neutral and then again water. The organic layer is then dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to yield ethyl 6-acetoxy-2-(ethoxycarbonylmethylthio)-phenylacetate as an oil.

Workup

  1. temperatureThe solution is heated to 100°
  2. additionAfter addition
  3. temperaturethe solution is heated until gas evolution ceases
  4. customthe solvent is then removed in high vacuo
  5. customto yield an oil which
  6. customThe layers are separated
  7. washthe organic layer is washed with water, saturated sodium bicarbonate until neutral and then again water
  8. dry with materialThe organic layer is then dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-681b77b092154d3a96ff6f156c3e0581
Source dataset
uspto-grants-1989_01
Patent number
US04801605

Reaction notes

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