6-Hydroxy-2-(3-nitrophenyl)chroman-4-one → 2-(3-Nitrophenyl)chroman-4,6-diol

HRID 31326Notes

Reaction equation

HRID 31326 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]=[C:32]([N+:36]([O-:38])=[O:37])[CH:31]=1)[CH2:24][C:23]2=[O:39]>>[N+:36]([C:32]1[CH:31]=[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:35]=[CH:34][CH:33]=1)([O-:38])=[O:37]

Participants

3

Reactant 2

HCID 179784866-Hydroxy-2-(3-nitrophenyl)chroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785222-(3-Nitrophenyl)chroman-4,6-diol

Procedure

2-(3-Nitrophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 6-hydroxy-2-(3-nitrophenyl)chroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.89 (br s, 1H), 8.29 (s, 1H), 8.20 (dd, 1H, J 8.2, 2.3Hz), 7.93(d, 1H, J 7.9Hz), 7.71 (t, 1H, J 15.9, 7.9Hz), 6.89 (d, 1H, J 2.8 Hz), 6.66 (d, 1H, J 8.7 Hz), 6.57 (dd, 1H, J 8.7, 2.9 Hz), 5.47 (br s, 1H), 5.33 (d, 1H, J 10.7 Hz), 4.88-4.92 (m, 1H), 2.33-2.39 (m, 1H), 1.83-1.92 (m, 1H).

Sources & evidence

ORD record
ord-af4a0e90a33d496b833985c363d38d34
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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