Water → Methyl {o-[5-(methoxymethoxy)-2-nitrophenoxy]phenoxy}acetate

HRID 21513Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[OH:15][C:16]1[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=1[O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH3:11][O:10][CH2:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH:7]=1)[O:15][C:16]1[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=1[O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-fluoro-4-(methoxymethoxy)-1-nitrobenzene (9.25 g, 0.046 mol), methyl (o-hydroxyphenoxy)acetate (8.5 g, 0.047 mol) and potassium carbonate (6.44 g, 0.047 mol) in N,N-dimethylformamide is stirred at 100° C. for 18 hours, cooled to room temperature, poured into water and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an orange gum. Flash chromatography of the gum using silica gel and a 35% ethyl acetate in hexanes solution gives the title product as a yellow oil (3.6 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

temperaturecooled to room temperature
extractionextracted with ether
extractionThe organic extract
washis washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto obtain an orange gum

Sources & evidence

ORD record: ord-24c530ac04374da9b6af1f2e14f1abda
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424280

Reaction notes

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