4-Chlorobenzaldehyde → Methyl 3-(4-chlorobenzoyl)pentanoate

HRID 462884Notes

Reaction equation

HRID 462884 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])=[CH:4][CH:3]=1.Cl[C:17]1C=CC(C=O)=C[CH:18]=1.C(OC)(=O)C=CCC.[C-]#N.[Na+]>CN(C)C=O.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]([CH2:17][CH3:18])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 8929Sodium CyanideHCID 230774Methyl 4-(4-chlorophenyl)-4-oxobutanoateHCID 519179Methyl pent-2-enoate

Product 1

HCID 20281503Methyl 3-(4-chlorobenzoyl)pentanoateYield 21%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

By the procedure described for the preparation of methyl 3-(4-chlorobenzoyl)propanoate (see Example 1), 4-chlorobenzaldehyde (22.48 g), methyl pent-2-enoate (13.65 g), and sodium cyanide (3.92 g) in dry dimethylformamide (DMF: 250 ml), followed by column chromatography on silica gel using dichloromethane: 40°-60° petrol (1:2) as eluent, gave methyl 3-(4-chlorobenzoyl)pentanoate (6.5 g, 21%) as a yellow oil.

Sources & evidence

ORD record
ord-058a3c3fcb4b4bbe89d9a3463b33cab7
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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