4-Nitrophenol → 4-nitrophenyl 4-nitrobenzoate

HRID 1158594Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:13]([C:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>C1COCC1.C(N(CC)CC)C.CN(C1C=CN=CC=1)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][C:19]2[CH:20]=[CH:21][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)=[O:9])=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: -30 °C

Procedure

8.77 g of 4-nitrobenzoic acid (52.5 mM) were dissolved in 400 ml of THF and 53.1 g of triethylamine (525.0 mM). The solution was cooled to −30° C. and 6.01 g of methansulfochloride (52.5 mM) were added dropwise. The mixture was stirred for 1 h at this temperature, then 6.95 g of 4-nitrophenol (50.0 mM) were added at once, followed by 250 mg of DMAP. The reaction mixture was stirred for 1 h at −30° C. and was allowed to warm to room temperature while stirred overnight. The next day, the reaction mixture was filtered, the cake was washed with THF and the filtrate was evaporated to dryness. The residue was purified by chromatography using silica gel and dichloromethane to give 11.0 g (38.2 mM, 76%) of 4-nitrophenyl 4-nitrobenzoate as white crystals.

Workup

addition6.01 g of methansulfochloride (52.5 mM) were added dropwise
stirringThe reaction mixture was stirred for 1 h at −30° C.
temperatureto warm to room temperature
stirringwhile stirred overnight
filtrationThe next day, the reaction mixture was filtered
washthe cake was washed with THF
customthe filtrate was evaporated to dryness
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-13655254972246efb612eb4fd62f87b8
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07811642B2

Reaction notes

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