1,5-Bis(4-methoxymethoxy-3-methoxyphenyl)-1,4-pentadien-3-one → 1,5-Bis(4-hydroxy-3-methoxyphenyl)penta-1,4-dien-3-one

HRID 77649Notes

Reaction equation

COC[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][C:13](=[O:28])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22]COC)=[C:18]([O:26][CH3:27])[CH:17]=2)=[CH:7][C:6]=1[O:29][CH3:30]>CO.Cl>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([CH:15]=[CH:14][C:13](=[O:28])[CH:12]=[CH:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[C:6]([O:29][CH3:30])[CH:7]=2)=[CH:17][C:18]=1[O:26][CH3:27]

Participants

Conditions

Temperature: 50 °C

Procedure

1,5-Bis(4-methoxymethoxy-3-methoxyphenyl)-1,4-pentadien-3-one (20j, 0.41 g, 10.0 mmol) was stirred in methanol (50 ml) for 15 min at 50° C. Concentrated hydrochloric acid (1 drop) was added and the solution stirred for 3 hr at 50° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a semi-solid. The crude semi-solid was purified by preparative thin layer chromatography with ethyl acetate/hexane to give 0.31 g (96%) of a yellow solid: mp 84-86° C. [expected mp 82-83° C.]; 1H NMR: δ 3.89 (s, 6H), 6.87 (d, 2H, J=8.4 Hz), 6.88 (d, 2H, J=15.9 Hz), 7.10 (m, 4H), 7.62 (d, 2H, J=15.9 Hz); 13C NMR: δ 56.1, 109.8, 114.8, 123.3, 123.4, 127.5, 143.0, 146.8, 148.1, 188.6.

Workup

customThe methanol was evaporated
extractionthe resulting residue extracted into ethyl acetate
washwashed with saturated sodium chloride
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customto afford a semi-solid
customThe crude semi-solid was purified by preparative thin layer chromatography with ethyl acetate/hexane

Sources & evidence

ORD record: ord-ea92152f73f6479ab7d3bb92e858f885
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841326B2

Reaction notes

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