ChemicalBook CAS DataBase List 4-Hydroxyphthalonitrile

4-Hydroxyphthalonitrile synthesis

9synthesis methods

Product Name:4-Hydroxyphthalonitrile
CAS Number:30757-50-7
Molecular formula:C8H4N2O
Molecular Weight:144.13

31643-49-9

30757-50-7

The general procedure for the synthesis of 3,4-dicyanophenol from 4-nitrophthalonitrile was as follows: 1) 103.9 g (600 mmol) of 4-nitrophthalonitrile and 800 mL of dimethyl sulfoxide (DMSO) were added to a three-necked flask equipped with a stirrer. After the solid was completely dissolved, 91.0 g (660 mmol) of potassium carbonate and 46.0 g (660 mmol) of sodium nitrite were added sequentially. The reaction mixture was heated to 160 °C and kept at reflux for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently poured into a large amount of water to precipitate the product. The yellow solid was collected by filtration and dried under vacuum at 110 °C to give 73.3 g of 4-hydroxyphthalonitrile in 85% yield.

31643-49-9 Synthesis

31643-49-9
462 suppliers
$6.00/5g

30757-50-7
130 suppliers
$60.00/100mg

23277-29-4
5 suppliers
inquiry

Yield: 0.098 g ， 2.451 g

Reaction Conditions:

with potassium carbonate;3-Hydroxypropionitrile in N,N-dimethyl-formamide at 40; for 99 h;Inert atmosphere;Molecular sieve;

Steps:

Synthesis process of 4,40-oxydiphthalonitrile (3)
3-hydroxypropanenitrile (6.3 g, 88.63 mmol) was dissolved indry DMF (125 mL) under nitrogen and 4-nitrophthalonitrile(5.08 g, 29.36 mmol) and molecular sieve 4? (10.80 g) wereadded. After stirring for 2 h, finely ground anhydrous potassiumcarbonate (13.50 g, 97.831 mmol) was added in portionsduring 3 h with efficient stirring. The reaction mixturewas stirred at 40 C under nitrogen for 96 h. The mixturewas then poured in to ice-water (300 g). The precipitate wasfiltered off, washed with water until neutral and dried. Thecrude product was extracted with chloroform (450 mL).The combined organic extracts were washed with water anddried with anhydrous Na2SO4 and evaporated to dryness.The resulting product was washed with water and thendried, yield 4,40-oxydiphthalonitrile (3) 0,098 g. The singlecrystals were obtained in DMF at room temperature viaslow evaporation. The other filtrate was acidified to pH 3with HCl and filtered off and washed with water until neutraland then dried, yield 4-hydroxyphthalonitrile (4)2.451 g. It was not necessary to purify the product more.The spectral specifications of 4,4’-oxydiphthalonitrile (3)and 4-hydroxyphthalonitrile (4) were consistent with literaturevalues.[27-32]

References:

Ery?lmaz, Serpil;Akdemir, Nesuhi;?nkaya, Ersin [Spectroscopy Letters,2019,vol. 52,# 1,p. 28 - 42]

31643-49-9 Synthesis

31643-49-9
462 suppliers
$6.00/5g

30757-50-7
130 suppliers
$60.00/100mg

References