2,6-Di-t-butyl-p-benzoquinone → HCID 20347432, compound

HRID 1701264Notes

Reaction equation

HRID 1701264 reaction equation
[C:1]([C:5]1[C:6](=[O:16])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:9](=[O:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]([CH2:19][CH2:20][PH:21](=[O:26])[CH2:22][CH2:23][C:24]#[N:25])#[N:18].CN(C)C(=O)C>O>[C:17]([CH2:19][CH2:20][P:21]([CH2:22][CH2:23][C:24]#[N:25])(=[O:26])[O:11][C:9]1[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]([OH:16])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)#[N:18]

Participants

5

Reactant 3

HCID 128672,6-Di-t-butyl-p-benzoquinoneHCID 31374DimethylacetamideHCID 178511210HCID 178511210, compound

Product 1

HCID 20347432HCID 20347432, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,6-Di-tert.-butyl-1,4-benzoquinone (11.0 grams; 0.05 mole) and bis-(2-cyanoethyl)phosphine oxide (8.0 grams; 0.05 mole) are dissolved in 20 mls. of N,N-dimethylacetamide and the solution is heated at reflux for 2 hours. The solution is then cooled to ambient conditions and drowned in water to precipitate a pale yellow oil which is subsequently separated, washed well with water, and extracted with diethyl ether. The ethereal extract is then stripped of diethyl ether and the residue is dried in vacuo at 50° C. to obtain 7.56 grams of a yellow oil which has an infrared absorption spectrum consistent with the desired product.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe solution is then cooled to ambient conditions
  3. customto precipitate a pale yellow oil which
  4. customis subsequently separated
  5. washwashed well with water
  6. extractionextracted with diethyl ether
  7. extractionThe ethereal extract
  8. customthe residue is dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-54f8408f056e4631b1474a09569d2f55
Source dataset
uspto-grants-1980_03
Patent number
US04192796

Reaction notes

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