Pyridine → 2-(4-t-Butylazo-4-cyanovaleryloxy)-2'-hydroxybenzophenone

HRID 442309

Reaction equation

HRID 442309 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:5].N1C=CC=CC=1.[C:23]([N:27]=[N:28][C:29]([C:36]#[N:37])([CH3:35])[CH2:30][CH2:31][C:32](Cl)=[O:33])([CH3:26])([CH3:25])[CH3:24]>CCOCC.O.CCCCC>[C:23]([N:27]=[N:28][C:29]([C:36]#[N:37])([CH3:35])[CH2:30][CH2:31][C:32]([O:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:5])=[O:33])([CH3:26])([CH3:24])[CH3:25]

Participants

7

Reactant 3

HCID 1049PyridineHCID 700382,2'-DihydroxybenzophenoneHCID 152740244-[(E)-tert-Butyldiazenyl]-4-cyanopentanoyl chloride

Product 1

HCID 227562192-(4-t-Butylazo-4-cyanovaleryloxy)-2'-hydroxybenzophenoneYield 71.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

To a solution of 4.68 g. (0.0218 m) of 2,2'-dihydroxybenzophenone and 2.5 ml of pyridine in 30 ml of ether in a 4 neck 100 ml round bottom flask equipped with a thermometer, condenser and magnetic stirring bar was added 5.0 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, 10% NaHCO3 solution and saturated sodium chloride solution. The ether was evaporated off leaving a yellow solid. The solid was slurried in pentane, filtered and air dried. The product weighed 6.3 g. (71.2% yield) and decomposed slowly on heating above 80° C. The infrared spectrum of the product was in agreement with the structure of the desired product.

Workup

  1. additionwas added 5.0 g
  2. customdid not rise above 25° C
  3. additionAfter completion of the addition the reaction mixture
  4. customThe ether layer was separated
  5. washwashed consecutively with 5% HCl, water, 10% NaHCO3 solution and saturated sodium chloride solution
  6. customThe ether was evaporated off
  7. customleaving a yellow solid
  8. filtrationfiltered
  9. customair dried
  10. temperatureon heating above 80° C

Sources & evidence

ORD record
ord-cbe8ee5b14404ad487ded47d33b5e99b
Source dataset
uspto-grants-1977_08
Patent number
US04045426

Linked notes

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