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

HRID 31276Notes

Reaction equation

HRID 31276 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([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:22][CH:21]=1>>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([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:22][CH:21]=1

Participants

3

Reactant 2

HCID 179785542-(4-Chlorophenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179786362-(4-Chlorophenyl)chroman-4,6-diol

Procedure

2-(4-Chlorophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 375 mg of 2-(4-chlorophenyl)-6-hydroxychroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.84 (s, 1H), 7.49-7.44 (m, 4H), 6.88 (d, 1H, J 2.8 Hz), 6.60 (d, 1H, J 8.6 Hz), 6.55 (dd, 1H, J 8.6, 2.8 Hz), 5.43 (bs, 1H), 5.14 (dd, 1H, J 11.9, 1.6 Hz), 4.87 (m, 1H), 2.26 (m, 1H), 1.85 (m, 1H).

Sources & evidence

ORD record
ord-e5e4bdb36f344cb082dac76bbb103abd
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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