Sulfuric Acid → HCID 12918689, compound

HRID 1758891Notes

Reaction equation

HRID 1758891 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7](=[O:19])[CH:8]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])C#N)C.S(=O)(=O)(O)O.C(OC(C)C)(C)C>O.C(O)(=O)C>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[CH2:8][C:7](=[O:19])[CH2:6][CH2:5][C:4]([OH:20])=[O:3]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7914Diisopropyl EtherHCID 12918688HCID 12918688, compound

Product 1

HCID 12918689HCID 12918689, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A 1-liter 1-neck R.B. flask was charged with 156.61 g (0.50 Mol) of ethyl-5-(2',4'-dichlorophenyl)-5-cyano-4-ketopentanoate, 153 ml of concentrated sulfuric acid, 153 ml of water, and 440 ml of glacial acetic acid. The reaction mixture was stirred and refluxed for 24 hours. The reaction mixture was cooled to room temperature and 300 ml of water added followed by 200 ml of isopropyl ether. The mixture was refluxed for 1/2 hour, cooled in an ice bath, and filtered. The desired acid (104.13 g, 80% yield) was obtained as a viscous dark-colored oil.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureThe mixture was refluxed for 1/2 hour
  3. temperaturecooled in an ice bath
  4. filtrationfiltered

Sources & evidence

ORD record
ord-7a8e9dea85a84a6989dfb7d98654fa7d
Source dataset
uspto-grants-1982_07
Patent number
US04338122

Reaction notes

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