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

HRID 31270Notes

Reaction equation

HRID 31270 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[F:19][C:20]([F:40])([F:39])[C:21]1[CH:26]=[CH:25][C:24]([CH:27]2[CH2:36][C:35](=[O:37])[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)=[CH:23][CH:22]=1>>[F:40][C:20]([F:19])([F:39])[C:21]1[CH:22]=[CH:23][C:24]([CH:27]2[CH2:36][CH:35]([OH:37])[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 179785102-(4-Trifluoromethylphenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785812-(4-Trifluoromethylphenyl)chroman-4,6-diol

Procedure

2-(4-Trifluoromethylphenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 860 mg of 2-(4-trifluoromethylphenyl)-6-hydroxychroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.86 (s, 1H), 7.77 (d, 2H, J 8.3 Hz), 7.68 (d, 2H, J 8.3 Hz), 6.89 (d, 1H, J 2.9 Hz), 6.63 (d, 1H, J 8.7 Hz), 6.56 (dd, 1H, J 8.7, 2.9 Hz), 5.45 (d, 1H, J 7.0 Hz), 5.26 (d, 1H, J 11.2 Hz), 4.90 (m, 1H), 2.32 (m, 1H), 1.85 (m, 1H).

Sources & evidence

ORD record
ord-3eabde3a767144aea6d4341ecd1a4694
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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