6-Hydroxy-2-(2-nitrophenyl)-chroman-4-one → 2-(2-Nitrophenyl)chroman-4,6-diol

HRID 31322Notes

Reaction equation

HRID 31322 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[OH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][CH:25]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N+:36]([O-:38])=[O:37])[CH2:24][C:23]2=[O:39]>>[N+:36]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH:25]1[CH2:24][CH:23]([OH:39])[C:22]2[C:27](=[CH:28][CH:29]=[C:20]([OH:19])[CH:21]=2)[O:26]1)([O-:38])=[O:37]

Participants

3

Reactant 2

HCID 179784666-Hydroxy-2-(2-nitrophenyl)-chroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785672-(2-Nitrophenyl)chroman-4,6-diol

Procedure

2-(2-Nitrophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 6-hydroxy-2-(2-nitrophenyl)-chroman-4-one. 1H NMR (300 MHz, d6-DMSO) δ: 8.87 (s, 1H), 7.99-8.02 (m, 1H), 7.77-7.86 (m, 2H), 7.59-7.64 (m, 1H), 6.89 (d, 1H, J 2.4 Hz), 6.56-6.57 (m, 2H), 5.51-5.55 (m, 2H), 4.85-4.92 (m, 1H), 2.42-2.47 (m, 1H), 1.85-1.96 (m, 1H).

Sources & evidence

ORD record
ord-1b2cd9a6c463471fbeae13e9c524c28c
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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