2-Nitrophenol → HCID 54451763, compound

HRID 1077390Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[CH3:21][C@@H:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[N+](C1C=CC=CC=1O)([O-])=O>>[CH3:21][C@H:22]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Reactant 3

HCID 69472-Nitrophenol

HCID 80080(R)-2-Octanol

HCID 185210364-(4-Methoxycarbonylphenyl)-2-nitrophenol

Product 1

HCID 54451763HCID 54451763, compound

Procedure

Methyl 4'-hydroxy-3'-nitro-4-biphenylcarboxylate 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-methylheptyloxy)-3'-nitro-4-biphenylcarboxylate (Compound 30, Scheme V, R1 =(S)--OCH(CH3)C6H13) as a slightly yellow solid after flash chromatography with hexanes/ethyl acetate [93/7]. Recrystallization from hexanes gave material with mp 69° C.; Rf [hexanes/ethyl acetate 90/10]: 0.23; 1H-NMR (300 MHz, CDCl3): δ 0.85(t, 3H, J=6.8 Mz), 1.20-1.52(m, 8H), 1.36(d, 3H, J=6.1 Hz), 1.62(m, 1H), 1.80(m, 1H), 3.92(s, 3H), 4.53(m, 1H), 7.12(d, 1H, J=8.7 Hz), 7.59(d, 2H, J=8.4 Hz), 7.72(dd, 1H, J=2.4 Hz, J=8.7 Hz), 8.02(d, 1H, J=2.4 Hz), 8.08(d, 2H, J=8.4 Hz); 13C NMR (300 Mz, CDCl3): δ 13.99, 19.46, 22.50, 25.19, 29.09, 31.65, 36.13, 52.17, 76.58, 116.07, 124.04, 126.53, 129.31, 130.35, 131.90, 132.06, 141.11, 142.81, 151.49, 166.75; IR (CHCl3): 3020, 2920, 2850, 1725, 1625, 1620, 1540, 1490, 1360, 1280, 1180, 1120, 1020, 820 cm-1 ; Mass spectrum m/z(rel.intensity): 385(M+ 47), 354(27), 273(100), 242(34), 139(17), 71(10) 57(20), 43(45), 41(38).

Sources & evidence

ORD record: ord-223ddd904a12431ebe4c86625ed1e15e
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05543078

Reaction notes

Loading…