1-Chloro-4-(chloromethyl)benzene → 1,7-Bis(4-chlorophenyl)heptane-3,5-dione

HRID 1655510Notes

Reaction equation

HRID 1655510 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1>>[Cl:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][CH2:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH2:5][CH2:13][C:12]2[CH:15]=[CH:16][C:9]([Cl:8])=[CH:10][CH:11]=2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 31261Acetylacetone

Product 1

HCID 197924821,7-Bis(4-chlorophenyl)heptane-3,5-dione

Procedure

Using 2,4-pentanedione (20.0 g, 0.2 mol) and 4-chlorobenzyl chloride (74.7 g), the reaction was carried out in the same manner as described in Example 17, (1), and the residual orange red semisolid (69 g) was recrystallized from methanol to give the title compound as s white prisms which was an ca 3:17 mixture of Keto/Enol as seen by the methylene singlet at δ3.51 ppm and the methine singlet at δ5.37 ppm in the 1HNMR spectrum; yield: 24.7 g; mp 74.6°-76.1° C.

Workup

  1. customthe residual orange red semisolid (69 g) was recrystallized from methanol

Sources & evidence

ORD record
ord-405db346cf5246e0a30395987029e860
Source dataset
uspto-grants-1993_10
Patent number
US05250669

Reaction notes

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