Nitric Acid → HCID 19696206, compound

HRID 863514Notes

Reaction equation

HRID 863514 reaction equation
[C:1]([CH2:4][CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)([OH:3])=[O:2].FC(F)(F)C(O)=O.[N+:22]([O-])([OH:24])=[O:23]>>[C:1]([CH2:4][CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:22]([O-:24])=[O:23])=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 12322879HCID 12322879, compound

Product 1

HCID 19696206HCID 19696206, compound

Procedure

A mixture of 2-carboxyethylindane (28.8 g, 0.15 mol) and trifluoroacetic acid (300 mL) was cooled in an ice bath and then treated with fuming nitric acid (50 mL). The reaction mixture was slowly warmed to room temperature and allowed to stir for 18 h. After removing the solvent, the residue was dissolved in an either:water mixture. The ether layer was separated and washed with water, and then saturated NaCl, and dried over magnesium sulfate. The filtrate was evaporated to give a dark syrup (34.3 gm, 3:1 ratio of isomers).

Workup

  1. temperaturewas cooled in an ice bath
  2. customAfter removing the solvent
  3. dissolutionthe residue was dissolved in an either:water mixture
  4. customThe ether layer was separated
  5. washwashed with water
  6. dry with materialsaturated NaCl, and dried over magnesium sulfate
  7. customThe filtrate was evaporated
  8. customto give a dark syrup (34.3 gm, 3:1 ratio of isomers)

Sources & evidence

ORD record
ord-3181199db3a74defa001e62f4c0593ca
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

Loading…