Pyridine → 4-(4-t-Butylazo-4-cyanovaleryloxy)-2-hydroxybenzophenone

HRID 442315Notes

Reaction equation

HRID 442315 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].N1C=CC=CC=1.CCOCC.[C:28]([N:32]=[N:33][C:34]([C:41]#[N:42])([CH3:40])[CH2:35][CH2:36][C:37](Cl)=[O:38])([CH3:31])([CH3:30])[CH3:29]>O>[C:28]([N:32]=[N:33][C:34]([C:41]#[N:42])([CH3:40])[CH2:35][CH2:36][C:37]([O:16][C:14]1[CH:13]=[CH:12][C:3]([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[C:2]([OH:1])[CH:15]=1)=[O:38])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 85722,4-DihydroxybenzophenoneHCID 152740244-[(E)-tert-Butyldiazenyl]-4-cyanopentanoyl chloride

Product 1

HCID 205634734-(4-t-Butylazo-4-cyanovaleryloxy)-2-hydroxybenzophenoneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4.7 g. (0.022 m) of 2,4-dihydroxybenzophenone and 2.5 ml. of pyridine in 35 ml. of ether in a 4 neck 100 ml. round bottom flask containing a thermometer, condenser and magnetic stirring bar was added 4.0 g. (0.0218 m) of 4-t-butylazo-4-cyanovaleryl chloride dropwise with cooling so the temperature did not rise above 25° C. After completion of the addition the reaction mixture was stirred 1/2 hour at room temperature and then diluted with 100 ml. of water. The ether layer was separated, washed consecutively with 5% HCl, water, and 10% NaHCO3 solution and saturated sodium chloride solution. The ether was evaporated off and the residue dissolved in methylene chloride, dried over anhydrous sodium sulfate, filtered and the methylene chloride stripped off under reduced pressure. The product weighted 8.8 g. (99% yield) and was a viscous syrup. The infrared spectrum was in agreement with the structure of the desired product.

Workup

  1. additionround bottom flask containing a thermometer, condenser and magnetic stirring bar
  2. additionwas added 4.0 g
  3. customdid not rise above 25° C
  4. additionAfter completion of the addition the reaction mixture
  5. additiondiluted with 100 ml
  6. customThe ether layer was separated
  7. washwashed consecutively with 5% HCl, water, and 10% NaHCO3 solution and saturated sodium chloride solution
  8. customThe ether was evaporated off
  9. dissolutionthe residue dissolved in methylene chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered

Sources & evidence

ORD record
ord-377ff4235c4f426e8a1745525d9ddae0
Source dataset
uspto-grants-1977_08
Patent number
US04045427

Reaction notes

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