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

HRID 31286Notes

Reaction equation

HRID 31286 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][CH:23]=[CH:22][C:21]=1[CH:26]1[CH2:35][C:34](=[O:36])[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([OH:37])[CH:32]=2)[O:27]1>>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]1[CH2:35][CH:34]([OH:36])[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([OH:37])[CH:32]=2)[O:27]1

Participants

3

Reactant 2

HCID 179785332-(2-Chlorophenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179786162-(2-Chlorophenyl)chroman-4,6-diol

Procedure

2-(2-Chlorophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 1.12 g of 2(2-chlorophenyl)-6-hydroxychroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 7.63 (dd, 1H, J 7.7, 1.8 Hz), 7.49 (dd, 1H, J 7.8, 1.4 Hz), 7.45-7.36 (m, 2H), 6.89 (d, 1H, J 2.9 Hz), 6.63 (d, 1H, J 8.8 Hz), 6.56 (dd, 1H, J 8.9, 2.9 Hz), 5.39 (dd, 1H, J 11.7, 1.5 Hz), 4.90 (m, 1H), 2.33 (m, 1H), 1.82 (m, 1H).

Sources & evidence

ORD record
ord-7698471d805b4ddcbbd364811467e013
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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