Nitric Acid → Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate

HRID 1713857Notes

Reaction equation

HRID 1713857 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[CH2:10]([CH:17]1[CH2:20][CH:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)Cl>[N+](C1C=CC=CC=1)([O-])=O>[N+:1]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH:17]2[CH2:20][CH:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18]2)=[CH:12][CH:13]=1)([O-:4])=[O:2]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 20313172Ethyl 3-benzylcyclobutanecarboxylate

Product 1

HCID 59464076Ethyl 3-(4-nitrobenzyl)cyclobutanecarboxylate

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A mixture of concentrated nitric acid (0.5 mL) and concentrated sulphuric acid (0.8 mL) was added slowly with stirring to an ice-cooled solution of ethyl 3-benzylcyclobutanecarboxylate (German Patent DE 2626287) (876 mmol, 4.02 mmol) in nitrobenzene (2 mL). The reaction mixture was warmed to ambient temperature and stirred for 1.5 h then poured onto ice/water. DCM (5 mL) was added and the mixture was stirred before passing through a phase separation cartridge. Solvent was removed by evaporation to give the title compound that was used directly in the next step.

Workup

  1. additionwas added slowly
  2. additionthen poured onto ice/water
  3. stirringthe mixture was stirred
  4. custombefore passing through a phase separation cartridge
  5. customSolvent was removed by evaporation

Sources & evidence

ORD record
ord-7fe7a60faf6743ef8546762ca605ea63
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…