6-hydroxy-2-(4-methoxyphenyl)chroman-4-one → 2-(4-Methoxyphenyl)chroman-4,6-diol

HRID 31330Notes

Reaction equation

HRID 31330 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]([O:36][CH3:37])=[CH:32][CH:31]=1)[CH2:24][C:23]2=[O:38]>>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([CH:25]2[CH2:24][CH:23]([OH:38])[C:22]3[C:27](=[CH:28][CH:29]=[C:20]([OH:19])[CH:21]=3)[O:26]2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 118180796-hydroxy-2-(4-methoxyphenyl)chroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179784492-(4-Methoxyphenyl)chroman-4,6-diol

Procedure

2-(4-Methoxyphenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 6-hydroxy-2-(4-methoxyphenyl)chroman-4-one. 1H NMR (300 MHz, d6-DMSO) δ: 8.78 (s, 1H), 7.35 (d, 2H, J 8.7 Hz), 6.94 (d, 2H, J 8.7 Hz), 6.88 (d, 1H, J 2.5 Hz), 6.56 (d, 1H, J 8.7 Hz), 6.52 (dd, 1H, J 8.7, 2.5 Hz), 5.37 (br s, 1H), 5.04 (d, 1H, J 10.9 Hz), 4.83-4.89 (m, 1H), 3.76 (s, 3H), 2.18-2.25 (m, 1H), 1.85-1.97 (m, 1H).

Sources & evidence

ORD record
ord-4f35db4ae9f2454488c634c571dff221
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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