Water → 4-(Benzyloxy)-2-hydroxybenzonitrile

HRID 1740488Notes

Reaction equation

HRID 1740488 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:18](CC)([O-])=O.C([O-])(=O)C.[Na+].O>C(O)(=O)C>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6587NitroethaneHCID 517045Sodium AcetateHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

Product 1

HCID 154532344-(Benzyloxy)-2-hydroxybenzonitrileYield 52.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 226 g (1.00 mol) of 2-hydroxy-4(phenylmethoxy)benzaldehyde in 287 ml (3.83 mol) of nitroethane and of 313 g (2.3 mol) of sodium acetate in 570 ml of acetic acid is heated at 104° C. for 8 hours and is then poured into 3 l of a mixture of water and ice. The precipitate is then filtered off, rinsed with diisopropyl ether and dried. 118 g of product are obtained. Moreover, the filtrate is extracted with diethyl ether, the organic phase is washed with an aqueous sodium hydrogencarbonate solution and then with water, dried over sodium sulphate and concentrated under reduced pressure and the residue is then triturated in diisopropyl ether. 67 additional g of product are thus obtained.

Workup

  1. filtrationThe precipitate is then filtered off
  2. washrinsed with diisopropyl ether
  3. customdried

Sources & evidence

ORD record
ord-41d13221f785483dbea59a1f481e9c6f
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

Loading…