6-Hydroxy-2-(3-hydroxyphenyl)chroman-4-one → 2-(3-Hydroxyphenyl)chroman-4,6-diol

HRID 1455044Notes

Reaction equation

HRID 1455044 reaction equation
FC1C=CC(C2CC(O)C3C(=CC=C(O)C=3)O2)=CC=1.[OH:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[O:27][CH:26]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=1)[CH2:25][C:24]2=[O:38]>>[OH:37][C:33]1[CH:32]=[C:31]([CH:26]2[CH2:25][CH:24]([OH:38])[C:23]3[C:28](=[CH:29][CH:30]=[C:21]([OH:20])[CH:22]=3)[O:27]2)[CH:36]=[CH:35][CH:34]=1

Participants

3

Reactant 2

HCID 122914786-Hydroxy-2-(3-hydroxyphenyl)chroman-4-oneHCID 179785602-(4-Fluorophenyl)chroman-4,6-diol

Product 1

HCID 179785322-(3-Hydroxyphenyl)chroman-4,6-diol

Procedure

2-(3-Hydroxyphenyl)chroman-4,6-diol was prepared as described for 2-(4-fluorophenyl)chroman-4,6-diol in Example 2(b) but starting from 6-hydroxy-2-(3-hydroxyphenyl)chroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 9.43 (bs, 1H), 8.88 (bs, 1H), 7.19-7.15 (m, 1H), 6.87 (d, 1H, J 2.7 Hz), 6.84-6.82 (m, 2H), 6.72-6.69 (m, 1H), 6.58 (d, 1H, J 8.7 Hz), 6.53 (dd, 1H, J 2.7, 8.7), 5.01 (d, 1H, J 11.3 Hz), 4.86 (dd, 1H, J 6.2, 10.8 Hz), 2.25-2.19 (m, 1H), 1.88-1.75 (m, 1H).

Sources & evidence

ORD record
ord-146dff202ce441f5befc9fe3b056cca4
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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