Benzaldehyde → 6-Hydroxy-3-methyl-2-phenylchroman-4-one

HRID 31203

Reaction equation

HRID 31203 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.[CH3:20]CC(C1C=C(O)C=CC=1O)=O.C(=O)C1C=CC=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][CH:7]=[CH:2][CH:3]=1)[CH:17]([CH3:20])[C:16]2=[O:18]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 703122',5'-DihydroxypropiophenoneHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Product 1

HCID 179784956-Hydroxy-3-methyl-2-phenylchroman-4-one

Procedure

6-Hydroxy-3-methyl-2-phenylchroman-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-dihydroxypropiophenone and 1.63 ml of benzaldehyde. The product was purified by column chromatography using heptane-ethyl acetate (3:1) as an eluant. 1H NMR (300 MHz, d6-DMSO) δ: 9.37 (s, 1H), 7.53 (m, 2H), 7.47-7.39 (m, 3H), 7.13 (d, 1H, J 3.1 Hz), 7.02 (dd, 1H, J 8.9, 3.1 Hz), 6.89(d, 1H, J 8.9 Hz), 5.17 (d, 1H, J 12.3), 3.18 (dq, 1H, J 12.3, 6.9 Hz), 0.84 (d, 3H, J 6.9 Hz).

Workup

  1. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-81f8b9c69ad04ed9a75bbaeb85c847cf
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Linked notes

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