n-PROPYL NITRATE → 2,4-Dibenzyloxybenzonitrile

HRID 322860

Reaction equation

HRID 322860 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P([O-])([O-])(O)=O.[NH4+].[NH4+].[N+:32]([O-])(OCCC)=O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[CH:13][C:10]=1[C:11]#[N:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12307n-PROPYL NITRATEHCID 24540Diammonium hydrogen phosphateHCID 18090802,4-Bis(benzyloxy)benzaldehyde

Product 1

HCID 103136042,4-DibenzyloxybenzonitrileYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2,4-dibenzyloxybenzaldehyde (1.59 g), diammonium hydrogen phosphate (3.5 g) and n-propyl nitrate (15 mL) in glacial acetic acid (5 mL) is refluxed for 15 hours. The reaction mixture is evaporated to dryness in vacuo and the residue is stirred with water (100 mL). The insoluble material is filtered and dried at 50° C. to yield 2,4-dibenzyloxybenzonitrile as a tan coloured solid (0.6 g, 40%), m.p. 100° C. [Elemental analysis:- C,79.8; H,5.47; N,4.48%. Calculated:- C,80.0; H,5.43; N,4.44%].

Workup

  1. temperatureis refluxed for 15 hours
  2. customThe reaction mixture is evaporated to dryness in vacuo
  3. filtrationThe insoluble material is filtered
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-9831dfc070f94d43ac3683f15f5f4b2f
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Linked notes

Loading…