2-Acetylhydroquinone → 6-Hydroxy-2-(2,6-Difluorophenyl)chroman-4-one

HRID 31300

Reaction equation

HRID 31300 reaction equation
FC1C=C(C2CC(=O)C3C(=CC=C(O)C=3)O2)C=CC=1.[OH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[C:28](=[O:30])[CH3:29].[F:31][C:32]1[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[C:33]=1[CH:34]=O>>[OH:27][C:24]1[CH:23]=[C:22]2[C:21](=[CH:26][CH:25]=1)[O:20][CH:34]([C:33]1[C:32]([F:31])=[CH:39][CH:38]=[CH:37][C:36]=1[F:40])[CH2:29][C:28]2=[O:30]

Participants

4

Reactant 3

HCID 102792-AcetylhydroquinoneHCID 1362842,6-DifluorobenzaldehydeHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Product 1

HCID 179784546-Hydroxy-2-(2,6-Difluorophenyl)chroman-4-one

Procedure

6-Hydroxy-2-(2,6-Difluorophenyl)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 2.6 ml of 2,6-difluorobenzaldehyde. The product was triturated from ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 7.55 (m, 1H) 7.22-7.18 (m, 2H), 7.14 (d, 1H, J 3.0 Hz), 7.03 (dd, 1H, J 8.9, 3.0 Hz), 6.93 (d, 1H, J 8.9 Hz), 5.84 (dd, 1H, J 14.0, 3.0 Hz), 3.38 (dd, 1H, J −17.0, 14.0 Hz), 2.80 (dd, 1H, J −17.0, 3.0 Hz).

Workup

  1. customThe product was triturated from ethanol

Sources & evidence

ORD record
ord-029755eaf6674aaa9055d0c61af1b24c
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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