2-Acetylhydroquinone → 2-(4-Fluorophenyl)-6-hydroxychroman-4-one

HRID 31290Notes

Reaction equation

HRID 31290 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.[F: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]([F:31])=[CH:2][CH:3]=1)[CH2:17][C:16]2=[O:18]

Participants

4

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 680234-FluorobenzaldehydeHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Product 1

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

Procedure

6-Hydroxy-2-(4-fluorophenyl)chroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 2.0 g of 2′,5′-dihydroxyacetophenone and 1.6 ml of 4-fluorobenzaldehyde. The product was recrystallised from acetic acid. 1H NMR (400 MHz, d6-DMSO) δ: 7.59 (m, 2H), 7.27 (m, 2H), 7.14 (d, 1H, J 3.1 Hz), 7.05 (dd, 1H, J 8.9, 3.1 Hz), 6.96 (d, 1H, J 8.9 Hz), 5.56 (dd, 1H, J 13.2, 2.8 Hz), 3.18 (dd, 1H, J-16.9, 13.2 Hz), 2.77 (dd, 1H, J −16.9, 2.8 Hz).

Workup

  1. customThe product was recrystallised from acetic acid

Sources & evidence

ORD record
ord-23465df4dcd94ce797be335283abd1be
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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