Nitric Acid → HCID 69650076, compound

HRID 2184210Notes

Reaction equation

HRID 2184210 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[OH2:10].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 69650076HCID 69650076, compoundYield 197.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 2-chlorophenylacetic acid (10.0 g, 58.6 mmol) in concentrated sulfuric acid (40 mL) was cooled to −10° C. and slowly reacted with a solution of fuming nitric acid (2.80 mL, 66.7 mmol) in concentrated sulfuric acid (7.2 mL). After 2.5 hours the reaction was slowly poured over ice water (400 mL), filtered over a coarse filter frit, washed once with cold water, and dried on the frit overnight giving the title compound (13.5 g, 98%) as a white solid. Integration of the proton NMR spectrum showed the product contained about 0.2 equivalents of 2-chlorophenylacetic acid, but thin-layer chromatography showed this to be inseparable from the product. 1H NMR (300 MHz, CDCl3/CD3OD) δ 8.25 (d, 1H, J=2.7 z), 8.13 (dd, 1H, J=8.7 Hz, 2.7 Hz), 7.61 (d, 1H, J=8.8 Hz), 3.89 (s, 2H).

Workup

  1. filtrationfiltered over
  2. filtrationa coarse filter frit
  3. washwashed once with cold water
  4. customdried on the frit overnight

Sources & evidence

ORD record
ord-73a6dfe99cee43b1b133873f4f795528
Source dataset
uspto-grants-2005_05
Patent number
US06900231B2

Reaction notes

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