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

HRID 31180Notes

Reaction equation

HRID 31180 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH:27]1[CH2:36][C:35](=[O:37])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=2)[O:28]1>>[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH:27]1[CH2:36][CH:35]([OH:37])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=2)[O:28]1

Participants

3

Reactant 2

HCID 179785862-(2,4-Dichlorophenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785882-(2,4-Dichlorophenyl)chroman-4,6-diol

Procedure

2-(2,4-Dichlorophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 1.2 g of 2-(2,4-dichlorophenyl)-6-hydroxychroman-4-one. The product was purified by column chromatography using heptane-ethyl acetate (2:1) as an eluant. 1H NMR (400 MHz, d6-DMSO) δ: 8.89 (s, 1H), 7.66 (d, 1H, J 2.1 Hz), 7.64 (d, 1H, J 8.5 Hz), 7.51 (dd, 1H, J 2.1, 8.5 Hz), 6.89 (d, 1H, J 2.7 Hz), 6.63 (d, 1H, J 8.7 Hz), 6.56 (dd, 1H, J 2.7, 8.7 Hz), 5.50 (d, 1H, J 6.8 Hz), 5.37 (d, 1H, J 10.4 Hz), 4.90 (m, 1H), 2.32 (m, 1H), 1.80 (m, 1H).

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-3f2c9e09f9a4491a87ef66bc254d7fbb
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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