2-Nitrophenol → (S)-methyl-4-(1-methylheptyloxy)-3-nitrobenzoate

HRID 2257441

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][C@@H:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[N+](C1C=CC=CC=1O)([O-])=O>>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([O:1][C@@H:16]([CH3:15])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

Reactant 3

HCID 69472-Nitrophenol

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

HCID 80080(R)-2-Octanol

Product 1

HCID 54524087(S)-methyl-4-(1-methylheptyloxy)-3-nitrobenzoate

Procedure

Methyl 4-hydroxy-3-nitrobenzoate was coupled with (R)-2-octanol using the same procedure as that given for alkylation of phenol 9, Scheme I, to give (S)-methyl-4-(1-methyheptyloxy)-3-nitrobenzoate (Compound 23, Scheme IV, R1 =(S)-OCH(CH3)C6H13). The product was purified by flash chromatography with hexanes/ethyl acetate (95/5) as eluent affording a yellow liquid, Rf [hexanes/ethyl acetate 95/5]:0.25; 1H-NMR (300 MHz, CDCl3): δ 0.82 (t, 3H, J=7.1 Hz); 1.14-1.50 (m, 8H); 1.34(d, 3H, J=6.1 Hz); 1.60(m, 1H); 1.75(m, 1H); 3.87(s, 3H); 4.57(m, 1H); 7.06(d, 1H, J=8.9 Hz); 8.11(dd, 1H, J=2.2 Hz, J=8.9 Hz); 8.39(d, 1H, J=2.2 Hz); 13C-NMR (300 MHz, CDCl3): δ 13.96, 19.31, 22.47, 25.06, 29.02, 31.60, 36.00, 52.35, 76.80, 114.63, 121.80, 127.17, 134.80, 140.27, 154.91, 165.08; Mass spectrum, m/z(rel.intensity): 309 (M+ 1), 197(32), 166(46), 112(48), 71(63), 57(100), 55(46).

Sources & evidence

ORD record: ord-17a261a958aa48d792a086645844ef89
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05658493

Linked notes

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