3-Hydroxybenzaldehyde → 6-Hydroxy-2-(3-hydroxyphenyl)chroman-4-one

HRID 1455043Notes

Reaction equation

HRID 1455043 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=1)[CH2:6][C:5]2=[O:19].[OH:20]C1C=C(C=CC=1)C=O>>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:20])[CH:13]=1)[CH2:6][C:5]2=[O:19]

Participants

3

Reactant 2

HCID 1013-HydroxybenzaldehydeHCID 179785412-(4-Fluorophenyl)-6-hydroxychroman-4-one

Product 1

HCID 122914786-Hydroxy-2-(3-hydroxyphenyl)chroman-4-one

Procedure

6-Hydroxy-2-(3-hydroxyphenyl)chroman-4-one was prepared as described for 6-hydroxy-2-(4-fluorophenyl)chroman-4-one in Example 2(a) but starting from 3-hydroxybenzaldehyde. The product was recrystallised from ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.50 (bs, 1H), 9.41 (bs, 1H), 7.22-7.17 (m, 1H), 7.11 (d, 1H, J 3.0 Hz), 7.03 (dd, 1H J 3.0, 8.9 Hz), 6.64 (d, 1H, J 8.9 Hz), 6.92-6.90 (m, 2H), 6.76-6.73 (m, 1H), 5.46 (dd, 1H J 2.9, 12.7 Hz), 3.09 (dd, 1H, J 12.7, 16.9 Hz), 2.75 (dd, 1H, J 2.9, 16.9 Hz).

Workup

  1. customThe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-668fe79ae8b444d88fcd2394309cb8c9
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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