Methanol → 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone

HRID 2101472Notes

Reaction equation

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

Participants

Reactant 2

HCID 887Methanol

HCID 138005Benzyl 2,4-dihydroxyphenyl ketone

Product 1

HCID 27756091-(2-hydroxy-4-methoxyphenyl)-2-phenylethanoneYield 88%

Procedure

Using the previous procedure and starting from 1-(2,4-dihydroxyphenyl)-2-phenylethanone (7.08 g, 31.0 mmol) and methanol (1.32 mL, 32.55 mmol), 6.60 g (88%) of the title compound was obtained as a white solid: mp 87-88° C. (lit. 92° C.); IR (KBr) 1635, 1620, 1589, 1437, 1350, 1291, 1230, 1206, 1127, 1021, 958, 802, 739, 729, 551 cm−1; 1H NMR (400 MHz, CDCl3) δ 12.71 (br s, 1H), 7.74 (d, J=8.7 Hz, 1H), 7.31-7.34 (m, 2H), 7.23-7.26 (m, 3H), 6.40-6.44 (m, 2H), 4.20 (s, 2H), 3.81 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 202.38, 166.61. 166.30, 134.82, 132.47, 129.76, 129.16, 127.50, 113.58, 108,27, 101.44, 56.00, 45.27.

Sources & evidence

ORD record: ord-1d167ce2bb5841b884bd608759c16188
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572919B2

Reaction notes

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