Nitric Acid → HCID 11097093, compound

HRID 876111Notes

Reaction equation

HRID 876111 reaction equation
[C:1]([C:5]1[C:6]([OH:19])=[C:7]([CH:12]=[C:13](C(C)(C)C)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].[N+:20]([O-])([OH:22])=[O:21].O>C(O)(=O)C>[C:1]([C:5]1[C:6]([OH:19])=[C:7]([CH:12]=[C:13]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 139874Methyl 3,5-di-t-butylsalicylate

Product 1

HCID 11097093HCID 11097093, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 3,5-di-tert-butyl-2-hydroxybenzoate (28.66 g, 108.4 mmol) was dissolved with stirring in 430 mL glacial acetic acid and the resulting mixture was treated drop wise with fuming nitric acid (90%, 179.26 mL). When the addition was complete, the resulting mixture was stirred for 2.5 h. The reaction mixture was poured into a 2.0 L of crushed ice and allowed to stand 30 min. Afterwards, 1.0 L of water was added and the ice water mixture was allowed to melt. The mixture was then filtered, washed with water and dried to provide the title compound (24.57 g, 89%).

Workup

  1. additionWhen the addition
  2. waitto stand 30 min
  3. filtrationThe mixture was then filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0af298bd2a7f4f06800d35575ec82c02
Source dataset
uspto-grants-2015_03
Patent number
US08986740B2

Reaction notes

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