4-Nitrophenol → Carbonic acid 4-Nitrophenyl (4-Nitrophenyl)methyl Ester

HRID 54803

Reaction equation

HRID 54803 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20]>O1CCCC1>[N+:29]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][O:21][C:19](=[O:20])[O:10][C:3]2[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=2)=[CH:28][CH:27]=1)([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformate

Product 1

HCID 21829967Carbonic acid 4-Nitrophenyl (4-Nitrophenyl)methyl EsterYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution, under argon, of 7.3 g of p-nitrophenol and 7.5 ml of triethylamine in 36 ml of dry tetrahydrofuran, is added, dropwise, a solution of 10.78 g of p-nitrobenzyl chloroformate in 18 ml of dry tetraydrofuran. The reaction mixture, a suspension, is stirred at room temperature overnight. The formed solid is collected, washed with water and dried to give 5.9 g of the desired product.

Workup

  1. customThe formed solid is collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-2e7fa016aefe4502be8c4ca49c30f83b
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Linked notes

Loading…