2-(3-Chlorophenyl)-6-hydroxychroman-4-one → 2-(3-Chlorophenyl)chroman-4,6-diol

HRID 31184Notes

Reaction equation

HRID 31184 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]2[CH2:35][C:34](=[O:36])[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([OH:37])[CH:32]=3)[O:27]2)[CH:23]=[CH:24][CH:25]=1>>[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]2[CH2:35][CH:34]([OH:36])[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([OH:37])[CH:32]=3)[O:27]2)[CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 179784992-(3-Chlorophenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179784902-(3-Chlorophenyl)chroman-4,6-diol

Procedure

2-(3-Chlorophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 730 mg of 2-(3-chloro-phenyl)-6-hydroxychroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.85 (s, 1H), 7.50 (d, 1H, J 1.7 Hz), 7.46-7.38 (m, 3H), 6.88 (d, 1H, J 2.5 Hz), 6.62 (d, 1H, J 8.6 Hz), 6.55 (dd, 1H, J 8.6, 2.5 Hz), 5.44 (d, 1H, J 6.6 Hz), 5.15 (dd, 1H, J 11.8, 1.4 Hz), 4.87 (m, 1H), 2.29 (m, 1H), 1.85 (m, 1H).

Sources & evidence

ORD record
ord-5faf5344fd3b4c0f80d64eade8e0cf2b
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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