Methanol → 1-(2-Hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone

HRID 2101474Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.[CH3:20]O>>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:20])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 887Methanol

HCID 259632Ononetin

Product 1

HCID 3547791-(2-Hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanoneYield 81%

Procedure

Using the previous procedure and starting from 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone (8.0 g, 11.0 mmol) and methanol (1.32 mL, 32.55 mmol), 6.8.5 g (81%) of the title compound was obtained as a white solid: mp 101-102° C. (lit. 104° C.); IR (KBr) 1637, 1611, 1513, 1459, 1346. 1301, 1237, 1174, 1148, 1026 797, 787, 626, 522 cm−1; 1H NMR (400 MHz, CDCl3) δ 12.72 (br s, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.17 (d, J=8.6 Hz. 2H), 6.86 (d, J=8.6 Hz, 2H), 6.40-6.44 (m, 2H), 4.13 (s, 2H), 3.81 (s, 3H), 3.77 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 202.73, 166.55, 166.27, 159.07, 132.42, 130.78, 126.73, 114.61, 113.53, 108.21, 101.42, 55.99, 55.67, 44.37.

Sources & evidence

ORD record: ord-e550916de76945fdae01fa4a53d27670
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572919B2

Reaction notes

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