Nitric Acid → HCID 22477756, compound

HRID 2064656Notes

Reaction equation

HRID 2064656 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH3:11])[CH3:2].[N+:12]([O-])([OH:14])=[O:13]>C(OC(=O)C)(=O)C.C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:12]([O-:14])=[O:13])=[CH:6][C:5]=1[CH2:10][CH3:11])[CH3:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 123975301-Ethoxy-2-ethylbenzene

Product 1

HCID 22477756HCID 22477756, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 1-ethoxy-2-ethyl benzene (3.5 g, Reference Example 51) in acetic anhydride (30 mL) was chilled in an ice-water bath. A solution of nitric acid (1.4 mL of 90%-30% excess) in acetic acid (25 mL) was added dropwise and the mixture was stirred overnight at ambient temperature. The reaction mixture was poured into ice water (300 mL) and the aqueous mixture was extracted with ethyl acetate (2×200 mL). The combined extracts were evaporated and the residue was chromatographed on silica gel (heptane with gradient of 5 to 10% ethyl acetate) to give 1-ethoxy-2-ethyl-4-nitrobenzene (1.4 g) as a clear liquid. LC-MS (Method E) RT=3.75 minutes, 196 (M+H)+.

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (2×200 mL)
  2. customThe combined extracts were evaporated
  3. customthe residue was chromatographed on silica gel (heptane with gradient of 5 to 10% ethyl acetate)

Sources & evidence

ORD record
ord-471d08f5d2ed4284a26bd427658d1ef7
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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