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

HRID 993396Notes

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

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 (2×) and the combined organic layers were dried over (Na2SO4), and solvents were evaporated. Recrystallization of the crude product from methanol/ethyl acetate gave 4-(4-nitrobenzyl)-benzoic acid (9.27 g, 58%) as a yellow solid.

Workup

temperatureThe suspension was cooled in a dry ice-acetone bath
additionThe reaction mixture was poured
custominto crushed ice
washThe separated organic layer was washed with dichloromethane (2×)
dry with materialthe combined organic layers were dried over (Na2SO4), and solvents
customwere evaporated
customRecrystallization of the crude product from methanol/ethyl acetate

Sources & evidence

ORD record: ord-cbb7ecdedccb4ae18195f1942e77eefe
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472536B1

Reaction notes

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