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

HRID 31318Notes

Reaction equation

HRID 31318 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][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)[CH2:24][C:23]2=[O:39]>>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]([CH:25]2[CH2:24][CH:23]([OH:39])[C:22]3[C:27](=[CH:28][CH:29]=[C:20]([OH:19])[CH:21]=3)[O:26]2)=[CH:31][CH:32]=1)([O-:38])=[O:37]

Participants

3

Reactant 2

HCID 179785166-Hydroxy-2-(4-nitrophenyl)-chroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785712-(4-Nitrophenyl)chroman-4,6-diol

Procedure

2-(4-Nitrophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) staring from 6-hydroxy-2-(4-nitrophenyl)-chroman-4-one. 1H NMR (300 MHz, d6-DMSO) δ: 8.86 (s, 1H), 8.26 (d, 2H, J 6.9 Hz), 7.74 (d, 2H, J 6.9 Hz), 6.89 (d, 1H J 2.8 Hz), 6.65 (d, 1H, J 8.6 Hz), 6.56 (dd, 1H, J 8.6, 2.8 Hz), 5.46 (d, 1H, J 6.9 Hz), 5.32 (d, 1H, J 10.5 Hz), 4.86-4.94 (m, 1H), 2.31-2.38 (m, 1H), 1.78-1.89 (m, 1H).

Sources & evidence

ORD record
ord-00902f9a5ec146278c91d0290d8286da
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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