Quinone → HCID 13901327, compound

HRID 918067Notes

Reaction equation

HRID 918067 reaction equation
[C:1]1(=[O:8])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.C(N(CC)CC)C.[CH:16](=[O:20])[CH:17]([CH3:19])[CH3:18]>>[CH3:18][C:17]1([CH3:19])[C:3]2[CH:2]=[C:1]([OH:8])[CH:6]=[CH:5][C:4]=2[O:7][CH:16]1[OH:20]

Participants

4

Reactant 3

HCID 4650QuinoneHCID 6561Isobutyraldehyde3×HCID 8471Triethylamine

Product 1

HCID 13901327HCID 13901327, compoundYield 90%

Procedure

A solution of 108 g. (1 mole) of p-benzoquinone in 1 liter of isobutyraldehyde is added dropwise with stirring to a refluxing solution of 500 ml. of isobutyraldehyde containing 5 ml. of triethylamine. The total addition and heating time is five hours. The excess isobutyraldehyde is stripped in vacuo leaving a crude oil that crystallized on standing. Trituration with cold chloroform gives 125 g. (70%) of product: m.p. 78°-81°C., nmr indicated the material to be 90-95% desired compound. A sample recrystallized from chloroform had a m.p. of 97°-99°C.

Workup

  1. additionThe total addition
  2. temperatureheating time
  3. customleaving a crude oil that
  4. customcrystallized
  5. customTrituration with cold chloroform gives 125 g

Sources & evidence

ORD record
ord-85f4057d261141979b030c01125ef641
Source dataset
uspto-grants-1976_07
Patent number
US03969372

Reaction notes

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