Hydroquinone → HCID 565258, compound

HRID 1248521Notes

Reaction equation

HRID 1248521 reaction equation
[O:1]=[C:2]([C:8]([O-:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:11]=[CH:12][C:13](=[CH2:15])[CH3:14].[C:16]1(C=CC(O)=C[CH:18]=1)O>C(#N)C>[CH3:15][C:13]1[CH2:14][C:2]([C:8]([O:10][CH2:16][CH3:18])=[O:9])([C:3]([O:5][CH2:6][CH3:7])=[O:4])[O:1][CH2:11][CH:12]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 6557IsopreneHCID 20976715HCID 20976715, compound

Product 1

HCID 565258HCID 565258, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 25.0 g of ethyl oxomalonate, 50 ml of isoprene, 80 mg of hydroquinone and 140 ml of acetonitrile were heated for 6 hours under nitrogen in a stainless steel bomb using an oil bath at 135° C. The reaction mixture was cooled overnight and the solvent evaporated. The resulting product was distilled at 120°-130° C. (0.7 mm Hg) to give 29.6 g of an oil, which was flash chromatographed on silica gel using 20% ethyl acetate in hexane as solvent. The resulting fractions 18-40 were evaporated and Kugelrohr distilled to give 26.45 g of the desired product as a mixture of regioisomers.

Workup

  1. customat 135° C
  2. temperatureThe reaction mixture was cooled overnight
  3. customthe solvent evaporated
  4. distillationThe resulting product was distilled at 120°-130° C. (0.7 mm Hg)

Sources & evidence

ORD record
ord-cc474f365e5c4195afc64df787ee3afa
Source dataset
uspto-grants-1985_06
Patent number
US04525203

Reaction notes

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