Ethanol → 2-Propen-1-one,3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)-

HRID 61961

Reaction equation

HRID 61961 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].O=[CH:12][C:13]1[CH:21]=[CH:20][C:18]([OH:19])=[C:15]([O:16][CH3:17])[CH:14]=1.N1CCCCC1.C([OH:30])C>>[OH:30][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:3](=[O:4])[CH:2]=[CH:12][C:13]1[CH:21]=[CH:20][C:18]([OH:19])=[C:15]([O:16][CH3:17])[CH:14]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1183VanillinHCID 8082PiperidineHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 2617062-Propen-1-one,3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)-

Procedure

2-hydroxyacetophenone (6.8 g, 50 mmol) was condensed with vanillin (7.7 g, 50 mmol) in ethanol (100 ml) and piperidine (8.5 g) at room temperature (20° C.) under nitrogen for 4 days to give 2′,4-dihydroxy-3-methoxychalcone. The crude mixture was filtered and the filter residue was washed with ethanol. The crude product (9.8 g) was stirred up with ethyl acetate and the intermediate product was filtered off (yield 8.3 g, 61% of theoretical). The intermediate product (2.73 g, 10 mmol) was then hydrogenated in ethanol (60 ml) using hydrogen at atmospheric pressure with the aid of a palladium catalyst on activated carbon (0.3 g, 10 wt. % Pd content, moist, water content ca. 50 wt. %), then filtered and the filtrate was evaporated to dryness, wherein compound 5 was obtained as a colourless crystalline material (2.3 g, purity >95%).

Sources & evidence

ORD record
ord-11bca0bd38624539ace044b5ee28b08e
Source dataset
uspto-grants-2016_09
Patent number
US09445606B2

Linked notes

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