4-Chlorobenzaldehyde → 2-(4-Chlorophenyl)-6-hydroxychroman-4-one

HRID 31275Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1.OC1C=CC(O)=CC=1C(=O)C.[Cl:31]C1C=CC(C=O)=CC=1>>[OH:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:4]1[CH:5]=[CH:6][C:7]([Cl:31])=[CH:2][CH:3]=1)[CH2:17][C:16]2=[O:18]

Participants

Reactant 3

HCID 77264-Chlorobenzaldehyde

HCID 102792-Acetylhydroquinone

HCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Product 1

HCID 179785542-(4-Chlorophenyl)-6-hydroxychroman-4-one

Procedure

6-Hydroxy-2-(4-chlorophenyl)chroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 3.0 g of 2′,5′-dihydroxyacetophenone and 2.8 g of 4-chlorobenzaldehyde. The product was triturated from ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.46 (s, 1H), 7.56 (d, 2H, J 8.5 Hz), 7.45 (d, 2H, J 8.5 Hz), 7.11 (d, 1H, J 2.8 Hz), 7.04 (dd, 1H, J 8.9, 2.8 Hz), 6.96 (d, 1H, J 8.9 Hz), 5.58 (dd, 1H, J 13.1, 2.9 Hz), 3.15 (dd, 1H, J −16.8, 13.1 Hz), 2.79 (dd, 1H, J −16.8, 2.9 Hz).

Workup

customThe product was triturated from ethanol

Sources & evidence

ORD record: ord-9ca15e25ac4f441eb610647bb50a0f6f
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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