Nitric Acid → 4-(4-Nitrobenzyl)-benzoic acid

HRID 1358830Notes

Reaction equation

HRID 1358830 reaction equation
[N+:1]([O-:4])(O)=[O:2].FC(F)(F)S(O)(=O)=O.[CH2:13]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[N+:1]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:20]2[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:27][CH:28]=2)=[CH:15][CH:16]=1)([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 62406Trifluoromethanesulfonic acidHCID 1364294-Benzylbenzoic acid

Product 1

HCID 218768784-(4-Nitrobenzyl)-benzoic acidYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

70% Nitric acid (3.16 mL) was added dropwise to a suspension of trifluoromethanesulfonic acid (9.34 mL, 105.6 mmol) in dichloromethane (250 mL). The suspension was cooled in a dry ice-acetone bath and a solution of 4-benzyl-benzoic acid (10.19 g, 48 mmol) in dichloromethane (50 mL) was added dropwise. The mixture was stirred for about 2 hours at −78° C. and an additional 2 hours at room temperature. The reaction mixture was poured into crushed ice. The separated organic layer was washed with dichloromethane (2x) and the combined organic layers were dried over (Na2SO4), and solvents were evaporated. Flecrystallization of the crude product from methanol/ethyl acetate gave 4-(4-nitrobenzyl)-benzoic acid (9.27 g, 58%) as a yellow solid.

Workup

  1. temperatureThe suspension was cooled in a dry ice-acetone bath
  2. additionThe reaction mixture was poured
  3. custominto crushed ice
  4. washThe separated organic layer was washed with dichloromethane (2x)
  5. dry with materialthe combined organic layers were dried over (Na2SO4), and solvents
  6. customwere evaporated

Sources & evidence

ORD record
ord-d930ba19d14e45e9945a950bbbdf4595
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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