2-(4-Ethylphenyl)-6-hydroxychroman-4-one → 2-(4-Ethyl-phenyl)chroman-4,6-diol

HRID 31200Notes

Reaction equation

C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[CH2:19]([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)[CH3:20]>>[CH2:19]([C:21]1[CH:26]=[CH:25][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:23][CH:22]=1)[CH3:20]

Participants

Reactant 2

HCID 179785782-(4-Ethylphenyl)-6-hydroxychroman-4-one

HCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785372-(4-Ethyl-phenyl)chroman-4,6-diol

Procedure

2-(4Ethylphenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 474 mg of 2-(4-ethylphenyl)-6-hydroxychroman-4one. 1H NMR (400 MHz, d6-DMSO) δ: 8.81 (s, 1H), 7.34 (d, 2H, J 8.0 Hz), 7.22 (d, 2H, J 8.0 Hz), 6.88 (d, 1H, J 2.8 Hz), 6.57 (d, 1H, J 8.6 Hz), 6.53 (dd, 1H, J 8.6, 2.8 Hz), 5.39 (d, 1H, J 7.1 Hz), 5.06 (d, 1H, J 10.7 Hz), 4.86 (m, 1H), 2.61 (q, 2H, J 7.6 Hz), 2.29 (m, 1H), 1.84 (m, 1H), 1.19 (t, 3H, J 7.6 Hz).

Sources & evidence

ORD record: ord-c43c66caab7a4f42a04818db30b469fc
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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