Vanillic Acid → 4-(Nitrooxy)butyl 4-hydroxy-3-methoxybenzoate

HRID 1895891Notes

Reaction equation

[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][CH2:22][CH2:23][O:24][N+:25]([O-:27])=[O:26]>CN(C)C=O.ClCCl>[OH:8][C:7]1[CH:9]=[CH:10][C:2]([C:1]([O:12][CH2:20][CH2:21][CH2:22][CH2:23][O:24][N+:25]([O-:27])=[O:26])=[O:11])=[CH:3][C:4]=1[O:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of vanillic acid (5.0 g, 29.73 mmol) in N,N-dimethylformamide (50 ml), cesium carbonate (9.68 g, 29.73 mmol) was added. The reaction was cooled at 0° C. and a 20% solution of 1-bromo-4-(nitrooxy)butane in dichloromethane (29.45 g) was added. The reaction was stirred at room temperature for 69 hours. The mixture was poured into a 5% aqueous NaH2PO4 solution and extracted with diethyl ether (3×70 ml) The organic layers were washed with water (70 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage System, Cartridge column FLASH 65+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 95/5 (500 ml), to n-hexane/ethyl acetate 1/1 during 4000 ml, n-hexane/ethyl acetate 1/1 (500 ml)). The product (5.88 g) was obtained.

Workup

extractionextracted with diethyl ether (3×70 ml) The organic layers
washwere washed with water (70 ml)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography (Biotage System, Cartridge column FLASH 65+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 95/5 (500 ml), to n-hexane/ethyl acetate 1/1 during 4000 ml, n-hexane/ethyl acetate 1/1 (500 ml))

Sources & evidence

ORD record: ord-1d15c53d90094d67ae1cac3b8034496e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518920B2

Reaction notes

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