6-Hydroxy-2-(3-hydroxyphenyl)chroman-4-one → 2-(3-Hydroxyphenyl)chroman-4,6-diol

HRID 31251Notes

Reaction equation

HRID 31251 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[OH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[O:26][CH:25]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=1)[CH2:24][C:23]2=[O:37]>>[OH:36][C:32]1[CH:31]=[C:30]([CH:25]2[CH2:24][CH:23]([OH:37])[C:22]3[C:27](=[CH:28][CH:29]=[C:20]([OH:19])[CH:21]=3)[O:26]2)[CH:35]=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 122914786-Hydroxy-2-(3-hydroxyphenyl)chroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785322-(3-Hydroxyphenyl)chroman-4,6-diol

Procedure

2-(3-Hydroxyphenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 6-hydroxy-2-(3-hydroxyphenyl)chroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 9.43 (bs, 1H), 8.88 (bs, 1H), 7.19-7.15 (m, 1H), 6.87 (d, 1H, J 2.7 Hz), 6.84-6.82 (m, 2H), 6.72-6.69 (m, 1H), 6.58 (d, 1H, J 8.7 Hz), 6.53 (dd, 1H, J 2.7, 8.7), 5.01 (d, 1H, J 11.3 Hz), 4.86 (dd, 1H, J 6.2, 10.8 Hz), 2.25-2.19 (m, 1H), 1.88-1.75 (m, 1H).

Sources & evidence

ORD record
ord-4b0cfd8a0d254b4c99309ab477cfc0b4
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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