Acetylacetone → HCID 19792539, compound

HRID 1655503Notes

Reaction equation

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

Participants

Reactant 2

HCID 31261Acetylacetone

HCID 78543(4-Chlorobutyl)benzene

Product 1

HCID 19792539HCID 19792539, compound

Procedure

Using 2,4-pentanedione (26.7 g, 0.267 mol) and 1-chloro-4-phenylbutane (110 g, 0.65 mol) obtained in Example 13, (2), the reaction was carried out in the same manner as described in Example 17, (1), and the residue was chromatographed on silica gel (Wako Gel C-200) with benzene/n-hexane (from 4:1 to 10:1) as eluent to afford the title compound as a pale yellow oil which was an ca 1:4 mixture of Keto/Enol as seen by the methylene singlet at δ3.52 ppm and the methine singlet at δ5.44 ppm in the 1HNMR spectrum; yield: 2.5 g.

Workup

customthe residue was chromatographed on silica gel (Wako Gel C-200) with benzene/n-hexane (from 4:1 to 10:1) as eluent

Sources & evidence

ORD record: ord-78d2cf831f974fb39df03a301cbe5552
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250669

Reaction notes

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