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

HRID 31207

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

Participants

Reactant 3

HCID 102792-Acetylhydroquinone

HCID 67970o-Fluorobenzaldehyde

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

Product 1

HCID 179785472-(2-Fluorophenyl)-6-hydroxychroman-4-one

Procedure

2-(2-Fluorophenyl)-6-hydroxychroman-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 1.4 ml of 2-fluorobenzaldehyde. The product was recrystallised from acetic acid. 1H NMR (400 MHz, d6-DMSO) δ: 9.45 (s, 1H), 7.67 (m, 1H), 7.47 (m, 1H), 7.32-7.25 (m, 2H), 7.14 (d, 1H, J 3.0 Hz), 7.04 (dd, 1H, J 8.9, 3.0 Hz), 6.95 (d, 1H, J 8.9 Hz), 5.77 (dd, 1H, J 13.5, 2.8 Hz), 3.26 (dd, 1H, J −16.9, 13.5 Hz), 2.76 (dd, 1H, J −16.9, 2.8 Hz).

Workup

customThe product was recrystallised from acetic acid

Sources & evidence

ORD record: ord-8f03d5fc26384c509562d6100f84af07
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Linked notes

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