Phenethyl bromide → HCID 19792517, compound

HRID 1655500Notes

Reaction equation

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

Participants

Reactant 2

HCID 7666Phenethyl bromide

HCID 31261Acetylacetone

Product 1

HCID 19792517HCID 19792517, compound

Procedure

Using 2,4-pentandione (93.8 g, 0.94 mol) and β-phenethyl bromide (405 g), the reaction was carried out in the same manner as described in Example 17, (1), and the crude product (350 g) was purified by column chromatography on silica gel (Wako Gel C-200, manufactured by Wako Pure Chemical Industries, Ltd.) with benzene as eluent to give the title compound as a pale yellow oil which was an ca 1:5 mixture of Keto/Enol as seen by the methylene singlet at δ3.43 ppm and the methine singlet at δ5.42 ppm in the 1HNMR spectrum; yield: 66.9 g.

Workup

customthe crude product (350 g) was purified by column chromatography on silica gel (Wako Gel C-200, manufactured by Wako Pure Chemical Industries, Ltd.) with benzene as eluent

Sources & evidence

ORD record: ord-66969afb0a8943b9a22d272c872913a1
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250669

Reaction notes

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